Re: Newbie seeks first boat advice
Kimper, yeah, it is fairly complicated isn't it! That's why you get the advice to rent for a while or buy used at leastuntil you really figure out what you want/need.
OK, now I'm going to solve all your problems by telling you exactly what you need!
You need a 19' open bow runabout with a 4.3L 220hp Volvo or Mercruiser power. (The 190 hp would work if it's a lighter, more shallow hull like the Stingray.) You want a captains seat with a flip-up bolster at least for the driver, no need for the passanger bolster. For your 1st boat experience i'd say middle or entry level used boat (see below for required condition). Glastron, Stingray examples of entry, Larson, Four Winns, Maxum examples of mid. Many others in both, but you get the idea.
Wake tower is worth about $1,000 extra IF you know you want one. Otherwise, aftermarket tower $1000 and very nice. Walk-thru transom nice, but certainly not needed. You Do want a swim platform, integrated one looks nicer, but same general function - most will have one I'd say in the boats you'll be looking at. Boat covers (made of Sunbrella or like) are expensive. $700 for cockpit, $400 for bow cover approx. IF they have them in great shape, that's a big savings vs. having new ones made. If you're trailering only you may want a trailering cover instead/also.
Look for a used, 2000-2002 model year. Try and spend below $15k. I did a search for these (not your area only, just FYI). Here's a few that fit the bill just fine. FourWinns middle/slightly above quality, then Stingray faster per hp and glastron cheaper brand. As you can see you can have plenty left of the $20k budget for operating cost, gas, etc. Keep in mind, these are ASKING price - expect to pay 10% less AT LEAST.
Also, if you look for a while you can find one that looks and runs VERY close to new in that age range. Do NOT compromise on crappy condition at all. Have a mechanic go over the engine/drive before paying. However, overall great condition usually means a well-kept engine as well. No rips/tears in upholstery, clean, orderly, nice looking gelcoat shine, etc. Also, a seller proud to show you his boat is a good sign!
http://www.ablboats.com/details.asp?ListingID=72286
http://www.ablboats.com/details.asp?ListingID=73486
http://www.ablboats.com/details.asp?ListingID=74658
Well, that's about all that I can think of. Oh...one more thing...OF COURSE I realoly don't know exactly what you want/need! This is, of course one person's opinion based on what you've said are your needs/wants/budget.
P.S. The dogs! They'll be fine except on very hot days. Get them little soft beds that fit under the console area for shade. Get a good dog PFD (yeah, silly, but important if they get near the sides. i though our dog would hate having one on, but he could care less.). Really rough or long days leave them home is all.