Wow, I went out of town for a few days and came back to find this thread still open.
Awesome.
Mr Bishop. As paranoid and ridiculous as it is for you to go around in disguises, here's another real question. What are you going to do about those fake license plates if you get pulled over for a traffic violation or have a fender bender and the police show up?
Also, your SO has a better chance of being suspicious when she accidentally runs across all the disguises and wonders why you have them. It's better to just go about your business and always have an explanation in your mind for why you are at such and such a hotel if you run into someone you know.
In all seriousness, the only thing I worry about is an STD. You can't disguise that. The rest is no problem if you are careful.