I've been communicating with a bunch of realtors inquiring about properties i see on the MLS and i feel like i'm all over the place not taking the proper steps to get to my goal. 

The fact that landlords and tenants respond to market factors does not make the Portland market free or efficient.

If you really hate to lose one of the month-to-month tenants you could offer a financial incentive to the new guy to terminate the lease and see where that goes.It sounds like your need to occupy one of the units was not communicated to the seller.

I would fly out to your area to verify all information and do a deal with you myself to make sure that your systems and processes are set up in a way that will be efficient for my clients.Look forward to speaking with you!

To calculate utility bills per square footage seems like a good estimate, but you can have the tenant that is efficient and likes to save power, while the other tenant blasts AC with the windows open and always has the lights/TV on.

Communication should be prompt and clear, you should be able to ask specific, detailed questions and get timely, data-backed answers.

New high efficiency mechanicals.

Since we live in the North most of the windows and doors have been changed to energy efficient ones.

For defaulted loans, my Servicer should be aggressive and understand methods to collect or disposition quickly and efficiently.  

Generally, they don't communicate very well, unless you are a bigger client.