You can find some decent boats on a shoestring budget like that... you'll also get a lot of experience and knowledge about how to maintain them, because they'll probably come from the early 70s and need a lot of maintenance
My boat, purchased a year and a half ago, is exactly the sort you're looking for. I find that on a yearly basis, moorage, maintenance, and insurance overwhelm the original cost of the boat.
Depending on where you live, for a small boat like that, your family might consider keeping the boat on a trailer on your property. A slip for a 22' boat can be over $2000/yr, and for 27' can be nearly $3000/yr. Insurance is comparatively inexpensive, so your other big cost is maintenance. If your family does all the work (and actually, two or three people is plenty to take care of a boat that size) then it can be a lot less expensive, but still: I've done all the maintenance on my boat and it's been about $1300 this year alone. Last year my total expenses were about $8K and this year we've been a bit more efficient at $4K, but I may have more projects at the end of the year.
To summarize, if you do all the labor yourself (and do it reasonably well), and you keep the boat in the water your biggest cost will probably be moorage. At least it was for me and I'm in a similar budget/boat range it would seem.