Another newbie heard from...
I'll chime in here as another n00b who's just now starting to get to that magic "tipping point" when straight shaving goes from losing a fight with a chainsaw, to becoming enjoyable and leaving me fairly smooth. I'm getting a good shave 4 days out of the week now, and trying to figure out where I'm inconsistent on that one day when it's not so good.
I'm sure due to my own stubborn nature, it's taken me far longer than it might have to get to this point: I first started trying with straights back in February, and it's only in the last two weeks that I am starting to get the "wow" going as I wipe off my face with a nice cool washrag.
My own stubborn nature is this: despite getting what is likely very good advice to send out my straights for expert honing, I was determined to do it all by myself. Thus, I was fighting both learning to hone and sharpen at the same time I was learning to shave with the straight. I bought a lot of expensive and fine tools for sharpening, including Lynn's excellent video, Norton stones and pasted paddles, but like you I was having a rough and sometimes bloody effort to get shaved.
I kept assuming the problem was an insufficiently sharp razor, when in reality face prep and shaving technique were the keys. That certainly doesn't mean I've mastered the art of sharpening, but it means that I've been at least "in the zone" on most of my attempts, but just didn't realize it due to poor technique.
Here are the nuggets that I would take away, one fellow newbie to another:
1. Face prep is absolutely essential. I shower, then use a hot washcloth over a pre-shave oil, then work in Proraso with a brush. There are many opinions, but my own experience is that the more you prep the easier the shave is. I'm sure there's a point at which diminishing returns make more face prep wasted time, but as of yet, the 3-4 minutes I spend steaming my face and working in oil and lather just keep giving better and better shaves, the more prep I do.
2. Stretch the skin. As I've seen mentioned, getting the jawline is particularly difficult for newbies, but if I shave my cheeks first, I can then use the fingers on my free hand to pull upwards on my cheeks quite a bit, thus dragging the skin over the jawline up and flat over my cheeks. Under the nose wasn't easy for me, either -- I've learned use the effective but ridiculous looking method of pulling up my nose with my free hand's fingers, first to one side and then the other, in order to allow the straight to lay closer to the skin on my upper lip.
3. For me at least, the only test that matters is shaving. Charlie Larman on this list was kind enough to point out, while delivering much excellent advice, that while many people use the HHT and it is meaningful for them, others can pluck themselves, their wives, and then their dog hairless trying to sharpen and resharpen to pass an HHT, with a razor that would give a perfectly good shave. Ditto for other "tests" that I've tried -- they just don't tell me, as a newbie, if I'm "there" while honing.
For a long time I used the test of shaving a small area on my forearms as a test, but it turns out that's also pretty meaningless. A good kitchen knife will shave my arms.
It's been a long, rough, and as I mentioned a mostly self-inflicted ride to get to where I'm having fun and getting results I like. Keith D'Grau at Hand American has also been very helpful with advice, and he makes excellent sharpening systems that are in my opinion easier for newbies to get a consistent result with than waterstones, along with some very fine strops.
KD