Jay,
I've tried everything. I have curly hair and it ingrows if you look at it funny - so I have to keep it really tight, every single day. It doesn't help that my fair Irish skin is extremely sensitive, too.
So, I've taken to a modification of the "barber shop" shave. I have a warmer for the lotion/gel, and I heat up a face cloth under EXTREMELY HOT water (175F at the tap), wring it out, and put it on my face before and after the shave. I use extremely hot water to rinse the razor, and rinse after every stroke, moving slowly with even pressure. I've found that most shaving lotions suck and only a few are good - Nivea, Edge Sensitive, and (I can't believe I'm saying this),
Aveeno Positively Smooth Shave Gel (which my wife uses). I started using it last year during cycling season (as most men's shave gels suck for shaving your legs) and tried it on my face, and it works great. Just have to put on some aftershave so I don't smell like lavender when I come into the office.
I've used the Gillette Fusion (you are from Boston, you must use their products
) ever since it came out, and I swap blades once a week.
Even then, my face still can look pretty bad. A straight edge razor isn't for the faint of heart and you can screw up your face real good with one. Floyd's 88 in Boston, plus King of Shaves in Back Bay, are great places to take one for a test drive and see how you feel / how you react.
Good luck!
Cheers,
-Andrew