The USB connection problem could be a damaged contact. Have you inspected them with a magnifying glass? Is the problem only apparent with just one cable, or one port?
If it's one particular port, it could be a dry joint (cracked solder) behind the port connector. If it's just one USB cable giving problems, it could be a wire broken internally. Have you tried swapping cables or ports?
The static thing has always appeared to me to be a little overblown. Unless you're wearing all-synthetic clothing, or you've been rubbing against synthetic upholstery material, I don't think it's something to be seriously concerned about.
I've always worked on my computers, built them, repaired them and maintained them, and never took any excessive steps to guard against static electricity, such as wrist bands or anti-static shoes. I rarely wear much synthetic clothing though, I own 99% natural fibre clothing.
I find the small brush head on the vacuum cleaner, operated in conjunction with a new, clean, 25mm paintbrush, works just fine on keeping keyboards, computer innards, and connectors clean.
If you think you may have a build-up of some kind that is preventing contact in the USB connectors, I'd be using a cotton bud dipped in an alcohol cleaner. Make sure the power is off to the computer before you commence cleaning operations.