Whats important is can they fulfill their initial promise to pay the monthly mortgage amount ... period.

I believe in giving them great customer service for fulfilling the terms of their lease to the fullest.

The contracts are so heavily tilted in favor of the sellers that you are essentially hoping they choose to fulfil their end and have no comeback if they don't.

The best part of it is yet to come...I'll be fulfilling one of my deepest desires with this mission.

This would bring me back to why UofH would possibly be of greater importance in that working professionals or professors w/ longer tenures would be more likely to fulfill the 30days as opposed to the 1 weeker tourist from Waikiki.

On the other hand, a group that has a deep bench of experience and a long time in the market and has built up their own net worth can fulfill every item on that list and then some. 

If exercise makes you happy/fulfilled do not sacrifice. 

Where can I find some good properties that might allow me to fulfill the aforementioned goal, am I going in the right direction?

Until I can fulfill that aspiration, helping people achieve their dreams of having a HOME for their families would be such an honor.

I think that if you are interested in gaining experience and knowledge then a passive investment would fulfill this goal, depending on who you invest with, regardless of how a future lender might view it.