(As a side note, the house isn’t really in terrible condition.

Taking the advice from Brandon turner he mentions you need to have your crystal clear criteria as this will narrow down and tune in what you should start looking for.My CCC would relate towards my goal of beginning my momentum train through house hacking1- primary residence, anywhere from single to four plex depending on if I have the capital to.2-It will be in the same city or nearby from where I currently work in Palmdale CA. 3- condition, not to sure to be honest if I get a fixer upper what repels me from this is not having to capital to fix it.

Given the current market conditions, you could have an easier time getting an accepted offer if you target properties that have been on the market for 2+ weeks instead of going after properties that are fresh on the market.

Unless I know the actual condition of the property, how do I know the actual cost?

Jacksonville HUD will normally reach out to you 60-90 days before lease renewal regarding new rental rates.Rental rates are normally dependent on amount of bedrooms / bathrooms and neighborhood.An inspector from HUD normally inspects the property before increase in rent to make sure property is in good livable condition.

Go Through Any Specific Tenant Requests or Conditions

--------------------------------What you save in heating bills in the winter you will spend on electric bills for air conditioning Spring/Summer/Fall.

What do you see as the major macro tailwinds and headwinds for purchasing residential small MF real estate under the current market conditions?

Next steps are inspections and financing conditions. 

I'm not sure how it works for VA, but for conventional loans, Fannie Mae specifically allows this if certain conditions are met.