First of all, I'll caveat everything I write below with it's really easy to spend someone else's money. Buying a boat can be a frustrating process, but you really should have fun with it. I looked for about a year, then eventually found what I wanted 500 miles away. Here's a couple of points to keep in mind (my opinions only):
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My d-day is tomorrow so any help is appreciated
Never give yourself a d-day. If a deal doesn't happen, more will come along. Surprisingly, I had 3 boats sold out from under me earlier this winter/spring before I found mine. Patience truly is a virtue.
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The 20k price point is good for me
The $20k price point without a trailer really means you are looking to spend ~$25k with a trailer, correct? Keep in mind a good trailer won't be cheap, especially if you're looking for a saltwater trailer. Based on a quick search on Boattrader, the $20k price point with a trailer is going to put you in the model year 2000 (plus or minus a few years) range.
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I fairly certain that in 2-3 years I'd be looking to trade to a newer boat, I guess this underpower issue may limit potential buyers and trade in value.
Do yourself a favor and do some research on boattrader (or any other similar site). Watch how the value drops on 10 year old runabouts. It doesn't seem to matter make or model, ~10 years seems to be a significant price drop point. Keep this in mind if you're looking at a 6-7 year old boat that you plan on trading in 2-3 years. That combined with the underpowered engine and you could take a decent hit. I bought a 5 year old boat this spring, but I plan on keeping it 10 years or more until my kids have moved on. Instead, if you're looking for a "starter" boat that you want to trade in a few years, maybe look for a clean late 90's boat to start with then work your way up from there.
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what does everyone think about the Mercruiser 350MAG Bravo 3, (300 HP) as compared to the VP?
I have no preference. I've owned both an found pros and cons in each. If you look hard enough you'll hear horror stories on both sides. Overall though, I think both are good drives assuming they've been well taken care of. I would stay away from OMC. I had some buddies that ran them in older boats and constantly seemed to have problems with them. That and I read on this site they can be hard to get parts for. In addition, for my money I would prefer a VP DP or Merc BIII drive for the size of boat you are looking at.
Once again, take your time. This isn't a race. I know this boating season is pretty much shot, but you're really getting into the right time to buy a boat. Even so, the right deal may not come along until next spring as it did with me.