If you come east on I-90 you'll pass 8 miles from me and if you come north on I-81 you'll pass 25 miles west of me. I-90 also brings you just a few miles from John Tennis (jatonka on SS) who usually has trucks for sale. Also, depending on your exact route you will be quite close to doghead who may have some prospects for you.
$5K spent wisely and patiently should get you a good truck. Unless you have the tools and mechanical ability to deal with potential major problems (or have a good MV mentor) you are most likely to be better off buying your first truck from a business or private owner than from a Government Liquidation auction. You will pay more up front than if you bought at auction but you'll be able to test drive it and get to know it before buying. The original buyer has taken a big risk and will expect to get paid for it but you will be buying a known item and not spending good money on something that may be uneconomically repairable.
From my experience a winch ads $1,000 to as much as $1,500 to a base truck and a hard top ads $500 to $800 to the price, more if the hard top is new. To put the hard top up charge in some perspective a new camo vinyl coated fabric cab cover will set you back a dead minimum of $250 and depending on the weather and whether the truck is stored indoors the top may only last a few years. Plattsburg gets a lot of snow. You are on the right track in wanting a hard top.
I have a couple deuces and a n M813A1 w/winch for sale so again, to help with perspective, I have a nice M35A2C (C=drop side bed) with a fully serviced winch and a hard top for sale. It has a few minor reliability upgrades, new clutch, dual spring base seats (M1009 bucket seat on the driver side), back up lights, pretty good rubber, fairly recent camo CARC paint and only 10K miles on a depot overhaul where it got a new engine, transmission and three new axles. It is for sale at $6,500. A lot of folks might think that's high, though.
However, up until about 7-8 years ago you generally had to buy two to three rough trucks from Government Liquidation that had probably been picked over for parts and then piece together a good truck from them. You usually had $8-9K in it.
Then there was a flood of M44 series trucks pushed out of the military inventory and these trucks were in a lot better shape than what had come before since they had gotten a lot better maintenance and parts funding due to the war. Most of the folks now in the hobby are fairly new and many think that the low prices from those few years are/were the norm. They weren't. Most folks who have been around MVs for 10 or more years will tell you that in many ways the last several years are very much the exception to the rule.
Another example is the CUCV family. Four years ago you could buy a running M1009 for around $1K if you were patient and a running M1008 for around $1,500. I bought a pile of them at thiose prices. But 10 years ago one would have cost 2-3 times that and now that only a few are auctioned off each week I'm seeing very rough M1009s go for nearly $3K.
Since so few M44 family trucks (which includes the M35A2) are being auctioned off prices are on the way back up. One thing is for sure though. They are still in service in the military services of a lot of other countries so parts will be readily available for many years.
If you are not sure what you want then you could do a lot worse than to go to a couple of rallys or major MV swap meets. You'll see a bigger variety of trucks and be able to ask questions of a lot more folks than you ever will any other way.
About what date are you moving?
I hope all this rambling helps.
Lance