Ton's of people with golden shackles of sub 3% rates, epic net shortage, skilled labor shortage, on and on. 

How do I know which questions to ask to ensure the property manager is performing at its best?

The best strategy I seem to have deployed so far was to contact all my current tenants and let them know I’d give them a cash referral fee of $250 for anyone they recommend to me that goes through the vetting process and successfully moves in.

From my understanding, no one is employed, they are somehow current with the rent, but they are definitely not someone I would offer a new lease...not even at market rate.  

I do my best to keep up with it and give them reliable information, but I'd really like a routine place to check each morning so I'm giving them the best and most up-to-date information possible.

Welcome to BiggerPockets Gabe and best of luck investing!

A lot of people tend to mingle these things when they talk about "break even" or "cap rate", but that leads to a lot of confusion.Let's use some real numbers which may be easier to understand. 

Retirement Account Contributions: Given my W-2 income and rental income, what are the best retirement accounts to contribute to for tax efficiency?

Elite’s rates are a little higher but they sound MUCH more flexible.

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?