Oh man, some great replies. Too many too individually respond to. You all came through much better than I could of hoped...both with the laughs and the actual suggestions.
Couple things:
1. I have a head sock thing made specifically for cold weather riding that is super thin, prevents this issues for the most part, but its too warm for anything except sub 65 degree weather. Plus it's a pain for shorter rides to work or whatever and adds one extra step to donning my gear...I already wear too much.
2. My RF-1000 is pretty soft indeed, but not soft enough for my girly man skin
3. I'm half Irish and definitely inherited these characteristics from that half. I shave with the grain, but the grain starts to go in every direction right about where the strap meets my under jaw and neck area...so this area gets irritated from shaving even when I don't ride. Someone call the whambulance.
4. You fuggers are funny
5. I think I like the silk sleeve or cut off finger from a soft glove ideas best as I don't want to commit to having to wear something around my neck or on my head/under my helmet. I do some super hot weather riding and plus it would be inconvenient.
6. I would love to grow a beard, and it would resolve this issue, but it looks too scruffy (again, the Irish thing) for the line of work I'm in.
I've been using the trimming side of an electric razor ever since and have never had a problem. Shaving side for the face (sans beard days) and trimming side for the neck. I got away with this through ROTC so I couldn't see it being a problem with your work.
Another thought: the straps on the Nexx X30 helmet are fully padded with nice, soft fabric on both sides, and uses what has become the standard European "quick release" buckle. It has a serrated tab that fits into the buckle mechanism like a ratchet, and it releases quickly. The strap length must be adjusted the first time it's used, but the serrations insure a small range of micro-adjustment when the buckle is secured.
This would surely take care of your problem as it is so soft I dont even feel the straps on my chin....
You should try shaving in a hot shower, I have to shave almost 365 days a year being in the military, and having to work most weekends, and ever since I started shaving in the shower I have had no issues. You can buy a mirror at walmart for $15 that hooks up between your shower head and the pipe that runs water over the back of the mirror so it never fogs. Best $15 I have ever spent.