There are many things to consider, and you'll get many different opinions here on AT. I assume that you're thinking about a midwest treestand type hunt as opposed to a western style or Canadian hunt? The best thing you can do is start talking to Outfitters personally and get a feel for who they are. There are so many out there now, that basically you'll need to narrow it down to a certain state or area that you want to hunt, set your budget and then start the research. Personally, I would look for a fully guided rut hunt with a reputable outfitter, as opposed to an unguided or self guided type hunt... the properties are generally much better managed and less pressured on guided areas. If a place like Iowa is on your radar I would start applying for the tags now and by the time you are back from deployment you may be able to draw the tag. It's a lot of money, so don't just take someones word, make sure you do the research yourself. When you start to narrow down your choices, make sure that you actually talk to the Outfitter on the phone or in person at a show... I think you can generally get a better feel for a person that way as opposed to hearing a bunch of fluff from the internet. Personally contact their references, both successful and unsuccessful hunters. Most importantly, set your expectations to a reasonable level. It doesn't matter where you are hunting, if it's free range it will be a challange. Mature bucks are not behind every tree like you see on TV, but to kill a 150" deer, the first step is to hunt where they live... but you will have to hunt hard to even possibly get an opportunity. Make sure that you are okay with the fact that you may come home without a buck in the back of the truck. Don't go after it like a "big buck" mission, treat it as a well deserved vacation and enjoy everything about the trip.