Hhmm, I never use a pointy iron tip anymore - never. Smallest I'll use is a smaller chisel tip. I only use chisel tip and bevel tip, and only Hakko brand.
https://hakkousa.com/products/soldering/soldering-tips.html?series=68
You need heat to get to where you want it and a wet flat surface works much better. By wet I mean wet the tip with solder - difference it makes is huge.
I haven't had much trouble bridging small gaps. Trick for drivers on brass pills is plenty of flux and hold the wet tip on the brass for a couple secs first - that's all you need to do to pre-heat it.