I've been lurking on this forum for almost a year, trying to learn something about boating and fishing. Fortunately, there are a lot of knowledgeable individuals who post on THT, and as well as a few who think that they are

, so I have learned a lot.
I live in the middle of Michigan, 2 hours from Lake Michigan (Salmon) and an hour and a half from Lake Huron (Walleye). I am planning to retire next year, and I have been looking for a boat to use in Michigan, from May through September, and in the Keys, from December through March. I am thinking new or almost new, with a budget of $50,000. What I need has to be comfortable in 2-3 footers, have enough room for three or four people, have the potential to go 20 miles offshore on nice days, and has to be small enough to trailer around Michigan and to Florida and back, every year, with a (5.3 liter) 1500 Crew Cab Silverado. My wife will be spending at least some time in the boat in Florida, so we won't always be fishing, and it would be nice if I could throw a fly from the boat.
I have looked at several boats, been stiffed by a couple of dealers, and have fallen in love with a Regulator 24FS. However, I cannot afford the Regulator, and I am bright enough to realize that it is too much boat for all of the trailering that I will have to do. I am now thinking of either a large (22-23 foot) bay boat (e.g., Scout 221, Cape Bay) or a smaller (21-22 foot) deep V. On Friday I am going to look at a (very slightly used) 2009 Contender 21, with a T-Top and an F250 Yamaha. On paper it seems to fit the bill, but.....
I'm looking for some opinions about this particular Contender, given what I am looking for in a boat, and would also be happy to receive any suggestions regarding any other boats which you think might work for me. Thanks in advance for your help.