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.

Repair Any Damage or Health and Safety Issues2.

--------------------------------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?

Also, if an unpermitted space isn't done in a "workmen like manner " the appraiser might call out the area's that are poorly put together if it's a safety or health issue.

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.

Once it will become too high pressure I will value my health more than the money.