For most of us getting a used boat would be the most logical choice. Finding a good one that doesn't require a lot of work is difficult. Restoration includes enhancing the dry land handling of the boat hence the use of boat dollies and storage boxes on trailers for equipment. Changing the running rigging sometimes is necessary. The goal is to make a boat safe, easy to set up, easy to get onto the water, easy to sail with controls that work well, easy to get off the water and back to the trailer or storage spot for tie down. There is a reason people give up on many activities. It is mostly because of all the work to get ready to do the activity. Concentrate on making this work as minimal as possible.
Sailing is a very worthwhile activity that you can't master even in a lifetime. There is always something about it that will remain a challenge.
All sailboats have their own specific inherent problems that experience with owning and sailing them will divulge. Many used boats have not had any maintenance, improvements or modifications done to them by their owner. If you aren't sure about market value do some research before laying out your hard earned dollars. You may be buying something that will need a lot of expensive replacement parts and repairs to make it sail worthy. Do some research and spend some time looking at boat yards if you can. Talk to knowledgeable people to help gain some perspective.
Remember, if restoring, upgrading or repairiing a sailboat, to check the class rules governing what is allowed for keeping the boat a one design for competition or other purposes. You may be required to use factory only parts or sails, etc.
Alberta Beach Catamaran Link to catamaran information sites.google.com/view/albertacatamaransailor/home
Laser Sailboat - Lots around but a bit costly to campaign on the race circuit due to the cost of sail replacements (which may be often) and spars that sometimes seem to bend too easily. New boats, if you can get one are getting expensive. A used boat (any sailboat) can have major structural problems that are not apparent when viewing. The internet will likely have articles or videos on what to be careful about when buying one. Gut wrenching in heavy wind and can be a handful when overpowered. May be called ILCA now. Positives include a lot of camaraderie in the group sailing this boat and there are a lot of really good youtube videos covering boat setups, laser sailing technique and other topics related to the laser.
Other choices for your money if buying new is the RS Aero. Better sail, lighter boat, everything about it is better. Still lots of Lasers racing in Alberta though.
Other similar boats include Bombardier Invitation, Byte and MegaByte, Force 5, and Banshee.
Hobie 16 - is a good design for Southern California where you need something to get you through the ocean surf easily and you can sail it right onto the beach when getting off the ocean. For lake sailing there are better catamaran choices for a two person catamaran lake sailboat. Best sailed with a regular knowledgeable physically fit crew and skipper. The boat is heavy to manhandle and easily tips over in just about every direction. Hobie 16's are very popular and generally there are a few used ones for sale.
Tasar - Well designed two person dinghy. Light weight, very lively sailboat. Won't stand up by itself so a dolly is almost mandatory. On the water the boat will tip over on it's own so you must be on board or have it in hand to manage it before getting under way. Cons include internal backing for bolts, screws, etc. is wood so these are likely rotten and need to be replaced with aluminum plate or some other non-rotting strong material. Check the hull/deck joint and make sure it is water tight. These are just a few of the potential problems besides needing a crew. If the boat has dacron sails these have been replaced with laminate sails (expensive) so if you are buying a used one try to get one with the newer sail system. There are a few Tasars around Alberta, some even in very good condition. New ones are horribly expensive. I really liked the two piece mast. It was easy to manage and I thought something other sailboat types should incorporate. 2
Tanzer 22 - I owned one for a number of years and there are lots of good things about this cruiser and a few not so good. This is where heavily built works well. Didn't like the scimitar rudder so I built a more upright one which greatly improved the steering (no more fatiguing weather helm that you had to counter steer). I probably should have kept this boat. Bad thing about this boat is the cast iron keel which rusts. I did paint it with epoxy and it stopped the rust to some degree. My boat had a swing keel which works well in Alberta Lakes. Cons include having to use a trailer extender to launch. Best kept at a marina slip to help get you going a lot faster. 1
San Juan 21 - Positives include popularity for racing, easy to launch (no trailer tongue extenders) and is lively to sail. If you dry sail the boat you will need a good trailer setup for launching and retrieval. Build a corral and support for the keel and some side post guides to help with retrieval from the water. Although it is long out of production spare parts are available. A braked winch for the pivotiing keel would be a beneficial accessory. 1
Sunfish - Easy sailboat to sail as the controls are simple. Easy to raise and lower the sail. Fairly light weight. Having a launch dolly would make it a nice package. Cons include the old sail system and the nearly deck sweeping boom. If you get one you can learn to sail with it and probably after awhile you will want to try something else. Usually used prices are reasonable and parts are available. Make sure you get a complete boat as some parts are very expensive. Spare parts still available and I believe new boats are available.
New Sunfish or board type sailboats as they are known, are still available. Look at the "Rocket" board type sailboat. The Rocket is a new sailboat available from Fulcrum Speedworks. The great things about this boat is the light weight and the fact it comes with a boat dolly all for the price of $4600 US brand new. Closest dealer however is Traverse City, Michigan. 2
Flying Junior - Good two person dinghy. Fairly manageable for a lighter weight crew. The boat has been around for a long while so there are many variations including models that have buoyancy bags (you probably don't want this model). Should be reasonably priced but you will have to be patient as they don't come up for sale all that often. Used boats likely need a fair bit of rejuvenation. The boat is still in production so spare parts should be available. 1
Sea Spray Catamaran - My own opinion, but probably one of the best small sailboats for single hand sailing. Downside is the work (worth it in the end if done right) required to draw out the potential of this boat. It is an excellent boat for fair competition. Class rules allow innovation which keeps the class up to date. Rolling your laminate sails and minimizing flogging will keep them in great condition for years. Works best with a launching dolly to help with on land boat handling, launching and retrieving off the water. There is a website under canadianseaspray.com for more information. Original models were lightly built for competition. Later models, aimed at the recreational sailor, are heavier and are more ruggedly built. Originally class minimum all up weight was 150 lbs but consideration for later models and their increased ruggedness/weight caused the class minimum weight to be raised to 180 lbs. Present day competition boat owners try to reduce weight on their boats to the 180 lb weight minimum. Improvements to the running rigging is allowed in the class rules. Also there is lots of latitude in daggerboard/rudder shapes and materials. Fairly easy to self rescue after a capsize provided you keep the mast sealed and maintain a good hull deck joint seal. 15-20
O'Day 20 - I had one of these years ago. It is a well designed small cruiser. I thought at the time it was pretty well built. It is definitely not a race boat but a pleasant enough boat to sail. I am not that familiar with the other smaller O'Day cruiser boats but they are probably pretty good as well. The swing keel models would work well on Newell if you find one you like. A low slung trailer may not need a trailer tongue extension to launch. 1
Trac 16 - Although heavy it is a fairly good two person lake catamaran with lots of buoyancy in the hulls. Good rudder system (no passing the tiller stick around the mainsheet block system). Problems include weak side stay anchor points (this should be beefed up) that can tear out if the boat is over stressed or over loaded in a big wind, broken parts may be impossible to replace (means you have to build your own) and will likely need a launch dolly to manhandle into the water. Potentially very fast in the right hands. 1
Santana 23 - water ballast. Sold it before sailing it and not sad about that. It was a compromise for the more race oriented Santana 23D (dagger board) sailboat that I always thought I wanted to have. I did look at a Santana 23D recently and glad to say now that I think I prefer the lighter, easier to manage SJ21. 1
Holder 20 - Lively/fast sailboat to sail if you can find one. The one I bought needed work that kept me busy for a long while. I sailed it a few times mostly to try to find bugs that needed working out. They are very good performance wise but when I did some research I found that they may not be the safest boats in a big blow. You might want to keep the cabin hatch closed up if the winds get up and you are overpowered. The cockpit is spacious but the cabin is very cramped. The trailer for this particular boat had roller bunks which I thought weren't very good. I tried to buy a new trailer and set it up with regular bunks but couldn't seem to find a suitable one. Local dealer couldn't get one so I was sort of frustrated and decided to sell the boat which in retrospect was a mistake. It is one boat that I should have kept. 1
505 - Challenging two person high performance dinghy. There are still a number of these boats around Alberta. You will need a competent crew and skipper to sail this type of boat well. The chance of finding one is good but expect to do some or a lot of work to keep it up. Sails and other parts would be expensive to replace. 1
Hobie 18 A good boat to bring along a friend or two. Lots of room on the tramp. A bit heavy but supposedly indestructible, it sails well and seems forgiving especially compared to sailing the Hobie 16.
Nacra 16sq. Winter Covid project 2021/2022. Working to make the boat easier to setup, launch, retrieve and easier to right from a capsize. Australian produced Nacra about 17 feet long and weighing about 300lbs. Uni rig but could be modified to fly a jib or asymmetrical spinnaker. Did some sailing with this boat. Pluses include light weight, good construction and buoyant hulls. A bit too large for me as a single handed boat. It does have enough room to take more people on board. Some regrets about selling it.
Ranger 20 This is a nice sized boat for Lake Newell. Well made and a nice design. Fairly local in the sense that about 600 were produced mostly in the Seattle area. If you are looking for one, keep an eye out in Washington state and various other states near Washington. Sometimes available in Alberta and BC as well. There is a Ranger facebook group for this boat and a couple of other Ranger models. Worth joining.1