Appreciate all the info again!
I do have various swr meters, dummy loads, different types of coax, plenty of connectors and termination tools, etc that I've collected in my time as a ham. Some of it will prove useful as I start tinkering on these cheap Cobra 29s I picked up from eBay.
I was definitely lacking in the DMM department, just cheap DMMs I've picked up up from walmart or amazon over the years. Fine for simple stuff, but nothing I'd trust to be accurate for much else, especially if working on radios. UPS guy should be delivering a Klein MM600 and a nice assortment of leads for it today. Definitely not a top shelf unit, but it'll do.
For soldering, just have a generic pencil style 110v and a Weller WLC100 that I've had for a few years and quite like. Again, not top shelf, but they work fine for what I use them for. No hot air station, and no experience there yet, but I'm intrigued enough to pick up a cheap station just to play around on some worthless PCBs.
As I mentioned earlier, I'm a hands-on learner and my biggest hurdle isn't so much the how, but the why. I can use a DMM and test a final, resistor, capacitor, test for continuity, etc. However, if you sat a no-rx or no-tx Cobra 29 down in front of me, no idea where to start, and if I did know which components to check first, parroting what I read or saw online, I wouldn't understand why I'm testing those components first and that is the downfall of relying on youtube or forum posts. I have a good head start in this field, more than the average joe, but achieving that level of fully understanding what this stuff is and why/how it does what it does is pretty much my only roadblock and I'm very much interested in getting to that point.