Re: Newbie begining first boat search.
If you want a summary: 20-21' would be great to start with.
If you have time, I spewed out a whole bunch below.
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OP, you only have 1 the kid?
Here's my experience.
Experience #1) 3.0L Mercruiser IO is 'ok' for skiing. Not a powerhouse, but it can do it. My family would ski with 4 of us in the boat (a Bayliner 185). Took a second or two to build up steam, but she went. Requires some additional driver skill, however, to prevent from sinking skiier or going too fast. If you just like being pulled on skiis, a few cuts here and there, it'll work. Overall space was OK. It had decent room & storage. We were young. 2-4 kids + dad. Closed water, small chop boat.
Experience #2) I had a Bayliner 175 last year (my own boat, first one), also with a 3.0L. Again, the 3.0L worked good enough for me to ski, wakeboard, tube with 4 people in boat. Mind you, I don't drop a ski. I can ski, and ski 'good enough', but I am certainly not a pro or doing any tricks. A 175 is small. 5 people was cramped because there wasn't a lot of storage space. I still had fun though. Gave me good experience from A-Z (maintenance, towing, launching, operating). More than a mild chop was annoying. For reference, I was 21 last summer, going out with my friends. Average weight would probably be 150.
Based on those 2 experiences, the following is my conclusion.
The 3.0L will work for skiing/wakeboarding. But, the question is, does 'will it work' cut it for you. It won't be 100% effortless. It won't rip at 100mph. Will it pull a skier with a full boat? Yes it will. Could you drop a ski? I don't know. I never tried.
Size matters. Yes, that's right. When I was younger, the 185 my dad had was fine. We fit, we were comfortable, we had fun. My 175, was too small. Also fun, but too small. This year I am looking to get a bow rider between 20-23 ft. The additional space will be great, but I am much more interested in the additional beam and draft. Tons of fresh water where I live. But, the wind can whip up a good chop. Would I take a 3.0L in a 20-23 ft boat? I would. My type of boating is I go out, I cruise, I drop anchor, I swim, lounge, play cards etc. Water sports are the minority of my time spent out on my boat (but I do enjoy them). I don't think any 20-23 footers come with a 3.0L. At this size they will at least be a 4.3 V6. Some 195's come with 3.0's, though.
With your budget, I think you could find a good 20-21' boat. Definitely something from 18-19ft will turn up. IMO, the prices this year are absurd. Don't know why, but everything is seriously overpriced. At least out here on the east coast. Maybe it is just me being too cheap, but I definitely have no intent of spending 7-9k on a 2001 Bayliner 185 (I've seen 4 different ones advertised on CL). If you're patient, the right deal will come up. This would be my other best piece of advice. Be patient. If the deal isn't there, well, the deal isn't there. I'm trying to buy a truck right now. I've seen a whole bunch - they all sucked. But every time I catch myself thinking 'well if I do this this and that, it would be OK...', simply because the prospect of a new purchase is exciting. I don't really want to do this this and that, but it would be quick gratification (reward now vs later).