As a fellow military guy, I can say without a doubt we are collectively the worst dressed group of people on the planet. Just look at any Friday safety brief held within the last 5-10 years for a confirmation. I can't tell you how many of my men don't even own a jacket or a tie and would consider putting on something with a collar for a date or an event some form of punishment. Why? The majority are under the age of 26. Even Field Grade officers and Command Sergeant Majors dress like crap. Why? They have spent all of their formative years in the military which means all day they wear a uniform and whenever they get off they throw on a unit t-shirt and some gym/cargo shorts or outdoors/adventure apparel or at worse some Affliction/Tap Out shit for the youngins. I think moving away from the PX and surfing blogs for inspiration is a good choice. Nothing good can come from the PX except polyester/rayon/fused sacks of shit. A $200 sack of shit is still is still a sack of shit no matter how many "designer" labels you slap on it.
Your chest waist drop is not unusual for the military, especially in our current CrossFit obsession. There are plenty of good "military tailors" around bases. These do not translate to good "clothing" tailors. Just because they can sew on patches and velcro while you wait does not mean they know how to do anything more than hem pants and jacket sleeves on dress blues/class A's. Don't be afraid to google around and drive away from post down towards Seattle to find a proper tailor. Say away from shopping malls near post. They universally sell crap. Nordstrom's in Seattle may have some decent stuff; but well fitting, quality staples from a department store sandwiched between a Hollister and a Hot Topic outside the post front gate are few and far between.
Sierra Trading Post is a great website to find high quality goods at huge discounts (Isia, Incotex, etc) I first started going to STP to buy extra Asolo hiking boots for Afghanismastan. Who knew? Hitting the AE/Alden seconds is a good plan. Stay away from boots until you get some decent balmorals/bluchers in black and brown. When I first started a wardrobe I bought a lot of "outfits" and "statement pieces". I was "hey this looks great on this posed online photo or on the mannequin in the store"-Avoid this. I filled my closet with a lot of junk that I can't wear with anything else that way. I found it was better to go with staples that can be mix and matched for versatility. (Try googling Put This On wardrobe essentials and the million other lists of 10 essentials for the wardrobe, etc). Classic, high quality, well fitting can never go wrong. A few of these with take you a lot further mixing it up than "outfits" and "statement pieces". Thrifting and eBay can be a good way to get a few essentials as long as you know a good tailor, avoid the "fuck yeah, I'm here to win" mentality of online bidding. Use Gixen or a sniping service and bid and leave it, you win awesome, you don't you didn't have to have it anyway or you'd have bought it in the store or "buy it now".
MTM will be good for you. I would start Navy, then Charcoal, then a mid-grey or glen plaid and go from there. Get a Navy blazer (dark horn buttons) that you can wear with your slacks or wear for business casual for the trips impromptu meetings. A few white shirts and a bunch of blue shade point collar and a blue OCBD and you'll be GTG for 90% of situations. Being well dressed with the basics is more important than power suits and power ties. Actually the phrase power tie makes me cringe at the thought of some loud, bright, garish tie as part of a costume with some ridiculous pocket square. You don't do costume well, you do uniform well. You know adhering to the rules and having your shit dress-right-dress is the best path to success. Follow this in your civilian dress. Well polished shoes, pressed clothes/shirt, straight gig line, and well tailored clothes are how you still pass the Board in the civilian world (see what I did there?). In the military, you were used to putting on all your flare as a walking 201 file so you could know a guy just by looking at him - "Hey look at my HALO wings or my CIB". Your temptation will be to mimic this with tie bars, pocket squares, flag pins, whatever -Avoid this. Quality, well fitted, well tailored clothes will make a much stronger statement than a "hey look at me" costume. Get comfortable with you're operating environment before you whip out your scuba bubble and ranger scroll combat patch (i.e. tie bar and pocket square) Same with your haircut - get rid of the high and tight(if you rock it full hooah like that) and go for well kept/well groomed professional. You're a grown man dammit wear a jacket. If you wear a tie, wear a jacket. For me, feel free to lose the tie if it's after the duty/work day, on the weekends, or you've got a drink in your hand.
The bottom line is it sounds like you are going to be working west coast, traveling east coast to do consulting/contracting for alphabet agencies, gov, and mil contract types. Think quiet professional - you know the ones I mean. The one who when he opens his mouth everyone shuts the fuck up and listens, not the pogue who can't wait to blab to you about his war stories from the Green Zone or Kandahar's boardwalk. You know to judge people on actions/deeds not words and that they weirdo no-last name with a beard and full Crye kit doesn't always know his head from his asshole, just like the quiet guy with fire in his eyes is not to be under estimated or taken lightly. Know your environment, if you're working with the people/organizations I think you're working with to secure contracts, they will be much more impressed by your hard, no-BS work ethic and that you know how to put yourself together with well fitting-classics than your designer suit and your "power tie".
Good luck with the start-up and the contracts. Remember "Hope" is NOT a method. Deeds not words.