It was really interesting reading Phil's "life story" and how he got into sound. I was a recording guy in my early twenties and got stuck doing sound for a musical for a community theater group in which my girlfriend was acting in. I was hooked immediately with the SR bug! I have now done 38 musicals (give or take) with various groups in the area. Oddly enough, the work seems to just be flowing in. Some of my sound friends are still out there banging gear around, slushing through the harsh winter load in-load outs, working until 3:00 to 4:00 in the morning, and making peanuts... while I'm sitting behind a Yamaha M7CL in a comfy sound booth from about 6:00 p.m. until about 10:00 p.m. making more money than they are.
My clientele are mostly high schools, community theaters, semi-pro theater, and then the occasional bar/venue gig.
I guess what I'm getting at is that there are other gigs out there than just bar gigs... even at your level. In fact, I've always thought that if you can learn to manage twenty wireless mics, three floor mics, four choir mics, and a fifteen piece orchestra (mic'd and piped in) while making untrained vocalist sound full and intelligible.... you'll have come a long way. I've built a niche market for myself and am generally the first call for most theater shows that need a sound designer. There aren't too many of us that specialize in theater sound! As for gear... I've gotten used to working with a multitude of mixers, effects, compressors, EQs, DSP, etc... that I wouldn't have access to otherwise. I've learned tons in the process!
Really, there is nothing wrong with wanting to build a rig and have nice gear, but it really does make sense to work for someone else (with their gear) so you can get better acquainted with what's out there. You'll still make some money while learning the ropes! As for building your own setup... reading reviews on gear is fun and rewarding, but until you actually play with something, you never really know if it's for you. I've certainly made gear choices for myself based on someone else's gear that I've worked with (or was forced to work with).
BTW- of all my gear choices (and there are many), I can say that the best ROI has been my 12 channel Audio Technica wireless set up and my $600 Mackie SDR hard disk recorder. Of course, these were bought out of necessity and I didn't salivate over these like I do amps, speakers, monitors, and mixers. Those two items are almost always out on rentals and make as much money as I make mixing.
Good luck and stay strong!