Get what you can afford both to purchase and to maintain. Do the very minimum required to get on the water. That's the objective. Doesn't matter if dirty or ugly, just will it take you somewhere. Don't postpone boating to work on cosmetics. There are alternatives. For the price range, there are boats that would be very enjoyable on lakes. Perhaps also staying on very protected waters. If what I could afford was a 20 year old, 19 ft Sea Ray Bowrider, then that's what I'd have and I'd be boating on it. There are many boats in my neighborhood that never leave the ICW. They're docked on canals and cruise the canals and rivers, primarily day trips. Sunday afternoon, they'll load up and go to a restaurant on the water for dinner.
Boating changes at every stage and age of life. What we're all forced to do is forget what we can't do, can't enjoy, and find that which we can. It might not fit our dreams. I don't know what it's like to be 80. I do know one thing though, it beats not getting old. For anyone 80 today, their life expectancy was 58 years if a male born in 1937. So celebrate 80. You didn't just win, you zoomed right past it.
And there also comes a time if we live long enough, boating just isn't practical. We can find a day cruise of some sort to satisfy the occasional longing. We can spend hours watching others and remembering all the good times we had. However, that's still all worth celebrating. I sure hope to live to 80.