I'm needing a better iron with some tiny tips for smd soldering, as well as general use and am wondering if I should buy used (Hakko or Weller, or a newer JBC if I get lucky) or wait and try to buy new.... Also needing a good multimeter (maybe not as expensive as a fluke but something that measures capacitance), power supply, Et cetera. This whole spending money thing is fun! Are Black Friday sales the time to buy?
Used is fine, so long as it's all there and it works (or if broken, actually repairable). Newer models tend to use MCU's or even custom chips, so there may be instances where a repair would mean buying a replacement board from the manufacturer.
DMM's that have a capacitance function can help, but the range tends to be limited and not all that accurate. Depending on what you need out of it, an LCR would be a better tool for measuring capacitor values IMHO.
There are non-Fluke DMM's that are decent.
Brymen would be worth a serious look IMHO, as they're well made and offer quite a bit of value (they get rebranded under names such as Extech and Greenlee, but tend to cost more this way). As a result, they're getting a lot of attention here in the forum lately. But they're by no means the only thing to look at (lots of threads, so a search should provide a lot of info).
Franky (iloveelectronics here on the forum), sells Brymen in his
store. Only a couple of models listed ATM, but if you contact him, I'm sure he'd be able to help out with your specific needs (what's coming & when, or if he can get a specific model).