Well about the whole, one woman man thing..... I heard a teaching once that it would be normal for men of any standing in that time and culture to have 3 women: your wife you married for position and family, your mistress was for fun, and then you had a favorite slave girl for convenience and all those things your wife and mistress weren't willing to do. If that be the case then Paul is really encouraging Timothy to pick men who stick to the much more restrictive practice we've come to accept that you don't have sex with people who aren't your wife and you only have one wife.
It's also possible to read this with slightly different punctuation so that it say something like "must be blameless: [all the specifics are how to discern if someone is blameless, not additional requirements]" in such case it would be much more if he's married this is how he should conduct his marriage and family rather than he must have these things (though in fairness an unmarried man probably wouldn't have the respect culturally to be chosen as a leader anyway).
It's also possible to read this with slightly different punctuation so that it say something like "must be blameless: [all the specifics are how to discern if someone is blameless, not additional requirements]" in such case it would be much more if he's married this is how he should conduct his marriage and family rather than he must have these things (though in fairness an unmarried man probably wouldn't have the respect culturally to be chosen as a leader anyway).