In my experience, the tiebreakers have all worked the way WIS "intended" them to. The way they intend them to work is stupid, but whatever.
See this thread
for a discussion with support on the topic.
Unsigned coaches are treated as if you have someone signed with a relevant rating of 0. So if the opponent has a coach with a relevant rating of 5 (really ******) he still wins. For pitchers, it is pitching coach and bench coach. For hitters, I'm unsure which coaches are considered. Probably worth a ticket to ask.
Also, what you listed above is the most restrictive contract, but not the "max" one for tiebreaker purposes. Unless the player demands the NT clause, for example, it does not impact the value of the deal.
Loyalty only matters if the FA was with the same team for the previous 5 seasons.
If loyalty is not a factor, I have never seen a player sign with any team other than the one with the "best" coaches (for pitchers, pitching and bullpen).