Most of the fixes I've had to made are either soldering a broken wire or changing a switch, both of which will require soldering skills. The rest have just been adjustments (mostly), reseating connectors etc. I've had both NIB and older 90's pins and there seems to be no difference in terms of maintenance frequency, the newest Sterns seem to have all sorts of issues due to cheaper components but that's just based on what I've read on pinside
I knew nothing of soldering when I started, so I ordered a couple practice kits from Amazon. I'm still not a pro, but I can get by and I'm not afraid to do that (thanks to the practice). Get good equipment though, if you have a sucky solder pump and a bad soldering iron it'll make even easy jobs difficult.
Also, you'll need some tools. There was a thread on that, but I can't find it.
Don't be afraid of the maintenance jobs, they don't happen that often and it's a great feeling when you successfully troubleshoot something (with help from pinside, if needed) and get it fixed. It's definitely a high!