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.

While the coming year might be ok (though very annoying), the fourth, assuming conditions are similar to today, will be difficult to see through.

Neither divorce lawyer nor the judge asked about their current living conditions?