Without reading through the whole thing.......I'd shop used and get a giggable setup now, go join a band and play music.
I can't imagine sitting around, with several opportunities to gig, and saying no to hold out for some "dream rig". Go get something that makes noise and play it. You can still save up for some fancy-schmansy and when you get there, flip this rig to help fund it or use it as backup.
You mention a custom bass and amp rig, so, do you have a bass now? If so, get some rig and play it. If not, how do you know what a "dream rig" is?