Here's the deal- you can buy a boat in great condition, or you can buy a bargain boat, but you will rarely find a bargain boat in great condition.
Boats aren't like cars:
A 40 year old car being sold by a little old lady in Florida who has owned it since new, always kept it in the garage, had it serviced every three months and only drove it to church on sundays is a great choice- low miles, no winters, well kept.
OTOH, A 40 year old boat in Florida being sold by a sailor who is no longer able to sail may be a great deal or it may be a pig in a poke. To be blunt, if the owner is too stiff and fragile to sail the boat, that sailor is also too stiff and fragile to keep on top of the maintenance. Likely that sailor has been slowly winding down for years, sailing less and less each year, which means that the boat may well be behind the refit curve. How many times have we seen here sailors who talk about planning to refit their boat for a cruise when they retire? Now, 10, 15, 20 years later that boat comes on the market. yes, the boat received new electronics, new sails, new canvas, new upholstery, had the deck hardware, hatches
, vents and ports rebedded and the engine rebuilt...
Odds are, some of it will need to be done again.
Can you get that boat at a price low enough to make the numbers balance when com[ared to buying a boat in better condition?
Yep...but usually only from the owner's estate, after it has languished on the market for years.
Sometimes buyers set the bar too high, trying to buy as much length and displacement as their budget will allow, and then finding themselves raiding the cruising kitty to cover expenses they hadn't figured into the boat purchase budget.
Frankly, I think you are underbudget for the boat you want and overboat for your intended use.
$50K will buy you a Cabo Rico, Tayana, etc.,
all are great boats, all are labour intensive- lots of wood, including spreaders, bowsprits, wood hatches
, wood rub rails, etc.
If you like boat puttering and are relatively handy, then these boats are a great choice. If you have to hire everything out because your spare time is limited and you want to leave work and sail, not varnish
or rewire, then add at least $10K to your purchase cost duriung the first year or less of ownership.
On the other hand, you can find lots of well fitted out "coastal" cruisers for under $50 k, needing less immediate work and with less ongoing maintenance as well.