Any boat will require maintenance, some to keep it working and some just to make it look pretty. You can decide how much you want to put into either side of the maintenance issue. A 50 year old boat is probably a way better deal than a 15 year old boat if it's been maintained. A 15 year old boat's systems, rigging, sails, motor etc. are quite possibly near their end of life cycle. The gelcoat may still be bright and shiny but there is a monster lurking in the details. An older boat that has been maintained will have renewed all the systems and may have many years of life left in them. Of course there is the older boat that is in the same state as the 15 year old boat less the brilliantly shiny gel coat. Sometimes even the gelcoat is fine on an older boat and still may function perfectly well even though it looks a bit dull. Look at the details of sailing the boat, living on it and basic cost of ownership rather the bright and shinies.
There are too many people on this list who think you need a bright shiny new condomarina before you can venture beyond the finger pier. Fine if you are rich, famous or just foolish enough to buy a newer boat. That's not to say that an older boat will be a deal but it will certainly be a lot cheaper initially than a much newer boat and in a lot of cases, way better suited to serious voyaging. The Cascades were mostly sold as kits and finished by the owners. Construction quality can run the gamut. The nice thing about the Cascades is the hulls are near bullet proof and even though the finish work may be crap, the boat will still be way safer at sea than a new plastic fantastic. Having said that, just because a boat costs $X doesn't mean that is all the money you'll ever put into it. It is very easy to double the initial investment if you insist on new sails, canvas, a paint job, totally redoing the interior to yacht quality and/or replacing the rigging. If you can't do the job yourself, plan it costing way more than double. On the other hand, if you can live with a not so great appearance, sails that are not optimum shape, limited hardware, etc, you may be able to own the boat for years without putting any significant money into it beyond bottom paint and safety issues like rigging. I know in my case, the money I've spent on the boat has been largely related to my ego. Have a bad habit of wanting the boat exactly the way I want it for single handing and 'looking good'. Would have put a lot of money into a newer way more expensive boat to get it equipped the way I wanted it as well as the plastic classic that I own.
If you have very limited experience, sign up for a course or two to get the basics and an introduction about being on a boat. If you have the time and inclination sign on as crew for a delivery to see what an extended period at sea is like. Sure there are crew positions available right now for deliveries down the Pacific Coast or back from Hawaii to the mainland. Be aware that these will mostly be DELIVERIES, getting the boat from point a to b the quickest and cheapest, though not easiest, way possible. Boats are often skinned out racers that may sail well but need a lot of bodies to make them go or boats that an owner doesn't want to sail themselves for various reasons. Accepting a berth on an owner sailed boat down the coast may be the best indication of what life at sea is about. Unfortunately, there are owners and there are owners so be sure you are simpatico before you get 10 miles out to sea. I've always been the type who goes whole hog into something and found it's the the fastest way to learn. Wanted to learn to sail so bought a Sailfish kit and built it myself when I was 12. Later bought a 26' boat to sail between the Islands in Hawaii. Bought a Westsail Kit, finished it out and sailed to SoPac and back. Current boat is a '69 Pearson 35 that I've pretty much reconstructed mostly to fit my personal whims. It hasn't been easy, lost the tips of four fingers on the Westsail, and not cheap but have never regretted the experience. One thing I have found out, if there is a will to accomplish something, I've always been able to make it happen.