G8YMW gave you some good ideas.

If you're still in SE KY, you're pretty far from large population centers.  So, it's especially vital that you get your antenna up high and run a little bit of power (maybe 100 watts or more).  Getting up on a hill with a beam of at least 6 elements during a contest will get you a lot of QSOs.  Another good time to try is Wednesday night nets.  KC9BQA (http://www.kc9bqa.com/) keeps a list of the active nets.  There is also a net called by KA1ZE/3 up in PA every morning on 144.205 MHz starting at 1200 UT.  This is a good time of day for tropo as we move into the summer months.

Turn it off and stick it in your carry on bag just like you would if you were driving in the car!

Just about every TSA inspector has seen a "walkie-talkie" before.  I'm reasonably confident that they can tell it apart from something that shouldn't be there.

Enjoy your trip!

I tried the DIY foam-in-place technique myself and had no real problems with it, but I would offer the following cautions:  1.  it takes a deceiving quantity of foam, 2. I don't know how much the mechanical properties of foam insulation differ from those of real foam-in-place material. 

I wouldn't really consider doing it myself again, but I would consider paying someone to do it.

A step bit works well if you have a drill press and the work will fit in your drill press.  (It sounds like this is the case.)  Otherwise, the knock-out punch is the way to go.  I have 1/2-inch and 5/8-inch Greenlee punches that weren't that expensive.  Is it not possible to bring your project to work or borrow the tools home?  I do this all the time.

I don't recommend QRP rigs as first HF rigs.  Unless you are so dedicated to the idea of QRP that you'll do nothing else, you should have the opportunity to try HF with 100 watts even if you never end up using it. 

Aside from that advice, nearly any HF radio produced by Yaesu, Kenwood, Icom, or Ten-Tec, in the past 20 to 30 years will be fine for a beginner if it has been well-cared for and not hot-rodded.  The best thing to, like AC4RD said, is to go try some of them out.

It's unlikely that a kit will save you battery, space, time, or money, in this application.  If you want to build a kit, that's fine.  But, it may be at odds with your other goals.  Many years ago, RadioShack sold a WX band receiver that was about the size of an altoids tin, complete with a telescoping whip antenna.  I have no idea how much it cost, but I'm sure you could find one at a thrift store or on eBay for next to nothing.

My Yaesu VX-3R is smaller than an altoids tin (and the aforementioned RS RX), has excellent battery life, receives a whole bunch of different modes/bands, and was very reasonably priced second-hand.  What's not to like about this?

Yup...standard four-digit grid is the exchange.  The ARRL January VHF contest usually experiences flat conditions on 6 meters, although you may get some aurora this weekend and possibly some sporadic-E, in addition to the usual meteors.  The June VHF contest is a blast on 6 meters, so if you have even a little fun in January, plan to get on in June.

Many non-smokers object to the odor of stale tobacco smoke that (rather quickly) attaches itself to radios and it changes the value of the radio accordingly.  In many cases, a film develops over the radio that's a bit difficult to clean up.  It's a matter of honesty in listing the sale.

If it doesn't matter to you, just ignore it, and you'll have access to more used radios!

The FT-530 was a great radio in its day.  But, there are a lot better choices now.  For example, I just replaced my Alinco DJ-580T with a Yaesu VX-3R...no comparison, the little Yaesu is head-and-shoulders above the DJ-580T.  Also, you might want revisit your interest in owning an HT.  VHF/UHF FM activity was much greater in many areas when you were last licensed than it is now...just wanted to make sure that someone mentioned that.

Some contesters use them.  But, I think cost is a major driver.

Agree with K9KJM:  the VX-3R is an awesome little radio that is very easy to program in the field.

If you are at a college or university (or even a high school), there may be requirements to be a "recognized student organization."  Usually there is an office at the school that specializes in helping hobby/special-interest groups to form.  They probably have template documents that you can use.  Interfacing with this office may be a good idea anyway if you eventually want to establish a station on campus, etc.  It often gives you access to a pot of money to buy equipment above and beyond member dues.  (Wonder why college tuition and fees are skyrocketing?  Here's a fine example.)

W5TFW is the manager.

Like KM3F says, there is a little bit of work to be done to figure out how to wire up a transverter. 

I prefer to use low-level split-IF (separate TX and RX lines from the IF radio at mW power levels) for a variety of reasons.  First, they are easy to switch.  Second, some exciters have a power spike when turned down to the 5-watt level to drive common-IF type transverters.  Third, most good HF radios have a rear-panel connection for low-level split-IF so I can leave the rest of the HF antenna systems undisturbed.  I know that the TS-590S can do this kind of operation without a lot of headache since I was looking into getting one to replace one of my TS-930Ses.

The big players in the transverter market are Down East Microwave and Elecraft.  Both are split-IF by standard configuration.  The Ten Tec is common-IF.  If you can find a working Microwave Modules transverter, they are usually a pretty good buy.  The final option is to roll your own, which I've done for six meters and will be doing for 432 soon.  It's not hard, but when I finished the six-meter box, I swore I'd never do it again.

The Maine OTH-B site has been decommissioned sometime during the past five years or so and the transmitters were sent to Arecibo for scientific use.  They are not yet up and running.

I have been to the west coast OTH-B transmit site just east of Christmas Valley, Oregon.  It's very impressive although only the buildings, fences, and ground planes remain.  The transmitters, antennas, and all copper, have of course been removed.