If cabling is a problem, make the cables. You'll get precisely what you need for the cost of switchcraft jacks and a spool of low capacitance coaxial wire. I can't imagine what would be so custom in a guitar rig that you can't make it yourself. Literally anyone can make a cable with some solder and electrical flux. And maybe, just maybe, some heat shrink. Even if you hadn't mentioned finances I would have recommend making your interconnects. It's not like you have a balanced signal or weird insert snakes. The core wire goes to tip, the screen goes to sleeve. If you have a ground loop make some cables with the screen detached at one jack and see if breaking the audio ground connection in a few places kills the buzz. You have a lot of gear and it may not all have the same ground potential. As long as your audio shields are all grounded at at least one place, preferably together you're good.
If you have to buy shock proof racks just bite the bullet and buy ATA approved cases. Nothing less will give you peace of mind. Cheaper cases aren't meant for heavy travel and especially not meant to house vacuum tubes on the road. Better to save money on DIY cables. I recommend Calzone cades if they're still in business. I haven't bought road cases in like 20 years.
Then you need to check you gear acquisition syndrome before it breaks the bank. Frankly your rig seems insanely excessive for you to be playing what you're describing as solo gigs in bars. I don't just mean that in a financial sense. A rig like yours is put together for 500+ seat venues.
If you really want a career playing guitar you should consider auditioning as a sideman for any style of music that can pay you and it's not hard to learn to read Nashville notation... your rig can handle more than prog metal. Go where the pay is.
Personally I was getting burned out on the whole thing when I was about your age (and my band was getting pretty successful until a lawsuit really kicked us in the ribs, but I was mainly hanging on for the studio) and I don't recommend pursuing it as a lifestyle but no one listens to middle aged dudes.
I have a behringer FC-whatever#s midi controller in my gear closet I'll sell for 50 bucks. Works fine once you program it... which isn't exactly fine, but that's midi rigs. I barely use it.