I would go:
Mondesi SP1,
Xavier SP2,
Ramsey SP3,
Estalella SP4,
James SP5
Osborne, Benard, and Martinez SuA
Handworth and Esposito SuB
Sutton LRA
Harper LHS (I don't think he's particularly good. This is the only role that I would keep him in the ML for.)
This is an interesting pitching staff. You're pretty short on long relievers/mopup (I would like to have three), but you've got four relievers who can each pitch 1-2 innings every day. I actually wouldn't mind having this staff at all. As for SP, I would choose to alternate them the way I did (I actually think Xavier is your best SP) in order for your 3 workhorses to give the bullpen a rest. If you dig up one more 30 stam/80 dur guy, I think you could actually go to a four-man rotation if you wanted to.
I'm intrigued by "Michael Jackson." I don't know what kind of numbers he would put out. If he has a long history of 4.00ish ERA, he might be worth signing. If he has more than a 4.30 or so in neutral parks, I would pass him over. "Tina Turner" would be better than Brad Harper.