Welcome to the forum!! You will get all kinds of advice here, most of it very good, even if it is not what you want to hear.
First off, Thank You for your Service!
Now my 2 cents worth..... From what I can gather from your posts, you don't even yet have an idea of what you want, and certainly not what you need. Slow down a bit, especially since you seem to thing you won't be buying for a bit due to market conditions improving. That may happen, and I think it will (buyer's perspective).
First step is look around at the many makes, model, and sizes of boats. Walk the docks, talk to boaters, ask questions about likes and dislikes, how they use their boat, etc. Try to talk to liveaboards for the pros and cons. Get an idea of what you like. At the same time think about what you want in a boat, especially with how you are going to use it in your mind. Make lists like: Must have features, Nice to have features, and Do not want features. For me (and boating can be very personal), a few things on my do not want list were: screwed down teak decks (leaks and can be maintenance heavy), exterior wood work (nice to look at but lots of work), and twin engines (cramped engine rooms, access for maintenance can be difficult, and more expensive to maintain and repair).
It sounds like you have not been on boats much. So get some training. There are boating schools, the US Power and Sail Squadron, etc. where you can do that.
Next, after you have a better idea of what kind of boat MIGHT suit you and your ideas of how you want to use it, charter a boat of that type. Tiltrider1 has given good advice about not buying first, but chartering. You might try the fishing trip idea ahead of the training part to get a feel for boat motion, etc. and to ensure that boating could be for you.
After all that, armed with your new knowledge about boating and especially how you plan to boat, you are as ready as you can be (in a relatively short time frame) to start looking at boats to buy.
This will ensure that you have the best chance to "be happy" with your choices. Doing much less, especially rushing in, will probably prove to be very expensive, and leave you at least somewhat unhappy.
As an analogy, take buying a car. All types out there. Do you need (want) a McLaren or a Honda Civic. Well depends on many things, but certainly on how you are going to use it! If you are mainly a commuter to work for a short distance with a couple of car pool friends, then the Civic wins hands down!
Owning a boat, especially an older boat that has had a questionable service history (most boats have little in the way of a service history in my experience), can end up being very expensive in either time, money, or both. Don't spend more than you need to.
Good luck.
This..! Welcome to TF. More advice than you can shake a stick at on here... 
