Based on the wording of your post, it appears you're passionate about Affordable and Workforce Housing, would that be true?

If that's the case and you aren't viewing more properties in person than you are making spreadsheets on, you are destined for analysis paralysis.Spreadsheets can only tell you estimations based on numbers given to you online or by a real estate agent whose job is to sell the property.

Based on personal experience, I would add assuring the lender is specifically authorized to perform an on-sight property inspection, at the lender's discretion / convenience. 

You do all of your own due diligence on what to offer based on the data.

I don't agree with your lender that you have to live in the property if you are using a conventional loan, but depends on what product they are giving you, maybe a work around for that.I would not purchase based solely on what income you can derive from STR.

I’m a real estate agent based in the vibrant Bay Area, specializing in helping clients find their perfect homes or investments.

Analyze and submit offer based on if you would have a 3rd party property manager.

Literally, there is no best option, only what fits your goals based on the info we know now! 

Hello BP,Wanted to reach out to get some opinions regarding Property Management Software that's recommended based on personal experiences.

Will you stay local and on base or have the potential to be deployed?