I think the biggest turn off - in-character-wise, anyway - to the proposal is the wording of:
- Wanted: Strong men of quality and courage to serve as my personal retainers for a lengthy trip East.
- Must have training in arms, at the least, as well as honor, good repute, character and learning.
Wynn is pretty sure that he doesn't meet the bolded criteria (and wouldn't be able to pretend for very long).
However, if word got to him that perhaps a more subtle approach was needed for certain activities, he'd probably be all for that.
[edit] And if we're only going to be testing out this setting for a couple of adventures (don't know how many sessions that might take), then I'm not going to worry too much about how much sense things need to make.