I've blown a bunch of $$$ boating. I don't regret a single penny of it. I'm really more just sad that it's basically going to be over when my youngest heads off to school this fall, and my only regret is that I didn't buy one when my kids were younger.
Buy a boat - but realize that you won't have more fun on a $30k boat (or $100k boat) than you would on a $5k boat. Go on Craigslist and find a good, used boat.
This is kinda true and kinda not. If you want to do towsports, and especially if you want to surf, the $5K boat is unlikely to be capable or safe. I think the pricepoints would be you won't have more fun on a $100k boat than you will on a $30k boat.
v-drive inboard with tower, ballast, perfect pass, reasonable number of hours is going to be $20K minimum (likely for a 21' boat) and up to $30-35 for a 23' boat. Even a decent sized direct drive with tower ballast and PP would be $15-20K.
And those would be smoking deal/winter/go get it right now prices. The good news is that boats at that age/pricepoint will depreciate very little if at all.