I was in the same situation, with regards to gear selection, last year. Here is what I started with, and what I've aquired so far. I shopped around for everything that I've bought thus far, and have only paid full retail for one item (kifaru guide lid). If you have the time to spend searching for deals, you'll be able to save a lot of money on quality gear.
Kifaru DT1, 2 med pockets, and guide lid - pack and pockets came from the classifieds here for a pretty good deal.
Salamon Quest 4d GTX - found an awesome deal but they didn't have my size. Called zappos.com and they price matched it.
KUIU merino base layers, chugach rain set, attack pants, yukon gaiters and down vest - 25% off on black friday
Thermarest neoair x-therm - found the large size discounted during 4th of July
MSR Reactor 1.0L - Heavily discounted during 4th of July sales
Black Diamond Carbon Z-lite poles - brand new on ebay for half price
Sawyer mini
MSR Dromlite 4L
The DIY forum on here has also saved me a lot of money. There is a ton of information on here about building your own gear. I'm in the process of building something similar to the mega tarp, and just got all the supplies needed to build a quilt using climashield apex 5.0. This past month or so, I've been making silnylon pullouts, stuff sacks, and meat bags. I was terrible at sewing when I first started, but I've built up my confidence with the little projects. My biggest concern is the shelter, and if mine doesn't workout, I plan on picking up a mountainsmith mountain shelter LT in the classifieds as backup. I've still got a few miscellaneous pieces to pick up, but I hope to have my gear list finalized in the next few months so I can let the roksliders tear it apart before my hunt.
Sorry for rambling, but this just goes to show that with a little patience and dedication, the buy once cry once attitude can still apply to those on a budget.