1) Expertise is generally a good feat if you're going to hit a bunch of times. So, it's really great for SMGs and ARs. Incidentally, a pistol build is one of the weakest in the game (by which I mean bullet pistols; energy pistols and chemical pistols are both superior) and if you play on a high difficulty you may have some trouble in parts. Pistols can be nice sidearms but they're not great primaries. If I had to pick between Expertise for a pistol build, and Quick Tinkering, I'd pick QT in a heartbeat. But Expertise has no requirements so all you'd need is a free feat slot for it, unlike QT which requires both stats and skills.
2) If you play stealth, yeah. If you plan to facetank hits, then Recklessness == reloads.
3) Tailoring will help you from the beginning of the game all the way to the end. Super Soldier drug will help you only at the very end of the game. I'd take tailoring, play the game a while, learn from your mistakes, then restart with another character, personally. But Super Soldier is amazingly powerful for the few seconds it lasts. It's just very, very, very, very, very, very scarce and getting the ingredients for it is a giant PITA.