In reply to xbraddersx:
> What is the best approach? Should I just continue to tackle S/HS and then the occasional VS and work from there?
Yup! You've already answered your own question, pretty much.
Speaking as someone who's been making a similar transition (predominantly indoor boulderer to trad climber), a few bits I can add:
You've probably got more than enough strength already, so what you need to focus on is learning and the mental side -- getting as much outdoor mileage as you can, working out how to get the hang of gritstone and practicing your gear placements.
In my experience, grit is the most different from indoor climbing, so don't be discouraged by that; you just have to put in the time to learn how to use it, and specifically practice skills you don't learn indoors, like all the forms of jamming.
(I got kind of fixated on getting on the least "indoors-y" routes I could find, because it's all the stuff I can't practice indoors. And this has served me well -- although it may be losing me climbing partners after I drag them up too many hideous offwidths ...)
If you're a nervous new leader, you need to spend as much time as possible leading. Drop the grade down as low as you need to feel that you've got a decent safety margin, practice your gear placements and build up your confidence (and expect to get hammered when the odd HVD or S will throw something at you that you've never encountered indoors).
Don't get fooled by "I can boulder [X] which translates in this table to tech grade [Y] therefore I should be climbing trad grade [Z]". Start every trip with some warm-up leads before you try to get on your "top" leading grade -- I find it takes a few routes for my brain to switch on, though that may just be me.
Lead lots and lots of Severes (and VDiff and HVD, which may sometimes feel harder) until it starts to feel comfortable, then lead lots of HS, then VS (and keep doing the Severes and Hard Severes!), and so on. Gritstone gives you so many wonderful classics at these grades, so it's not a hardship -- take your time to enjoy the scenery on the journey, so to speak. The UKC logbook is useful here just as a way of seeing how much volume you're building up, and how wide the base on your route pyramid is.
Don't fixate too hard on "HVS by the end of the summer"; it's nice to have a goal, but you've not "failed" if you're making progress and learning and enjoying yourself but haven't hit HVS just yet.
If you chose, you could pick an HVS (maybe one you've already seconded), put a top-rope on it, work it to death then headpoint it, and you'd technically have "done an HVS" -- but it wouldn't have improved your skills as a trad leader at all. Personally I wouldn't choose that approach.
> I've been terrified on quite a few grit S/HS
That will happen ...
(Looking at your logbook -- was one of them Grey Slab, by any chance? Because it *is* a gearless thrutchstravaganza.)