I'm sure I'd be on your list as not a good player with to many basses and guitars. I have a feeling lots of great players are also on your list like John Entwistle & Kip Winger.
I've only been playing 3 years and have about 9 basses. I'm sorry I have more than my ability rates with you. I'm not a great bassist, but I am getting better every day. Why do I have so many, because I'm one that jumps on a tremendous deal when I see one. Not every time, but if it's something I like and the price is stupid low, I'll probably end up buying it. The same reason I have so many guitars. When grunge hit, no one wanted the big hair Kramers, I was buying $1000 guitars for sometimes as low as $100. I bought as many as I could afford, now they're up into good money again. I didn't necessarily buy em to make money, I just dig em. If they're bringing money now that's a plus for me, but I'm not selling. They'll probably be extra money for the wife when I'm gone. The basses were just great deals on CL, I could afford them and I jumped on the deal. Most were around $100, I've never broke $300, and that's only a couple, all nice basses.
I find it hard to believe collectors have kept you from getting an instrument. If you want something it's out there. Sure a 65 Precision is gonna cost you, that how old rare things work.
I didn't join TB to make friends, but I have. I love the fact I have friends I made here from around the world.
My older brother is probably comparable to you skill and gig wise, probably bigger. I was in a battle of the bands over the summer (I know, not my idea) but it was one of the bigger things I've done in my 3 years as a bassist. I called my brother to see if he had any advice, he told me to "Have Fun" that's what I did and continue to do. You should try it sometime, feels pretty damn good. I want things to be right, but I'm not gonna go thru all this to play and not have fun.
Sincerely a Mediocre Bassist "with to many basses",
Peace N Chicken Grease