Not sure about where you're looking, but anywhere in Colorado here, if the home is zoned single-family then you can rent that separate space I'm talking about as long as you live there, but as soon as you move out, you can only rent the whole home as one unit.The trick then is to find a SFH with a potential separate entrance to the basement that is zoned multi-unit.

You want to invest just to have a place to live and potentially offsetting your mortgage payment by renting out the vacated rooms or having x amount of cashflow in the future?

Your response will then dictate potential methods to transfer wealth.  

It also really helps to have an experienced VA lender on your team like @Zack Karp who can help you avoid & navigate potential problems.

Billboards are new animal to us & their potential is a gray area to me. 

You want to have a discussion whether the property is considered 'active' or 'passive'If it is active, you can potentially accelerate the losses to offset your other forms of income.

It is potentially possible that a scenario would not get automated approval through Fannie's automated system call Desktop Underwriter (DU/DO) at 75% but would at 70% but again if that was the case it should be explained that way.  

Yes, it is possible to get a cost segregation study on a property placed into service in the past.There is potentially a requirement to file form 3115 which basically says that you screwed up the depreciation in the past and are therefore recalculating it.

Here is a trend I am seeing in all markets....COVID and Post-COVID era STR owners are selling because of many reasons (headaches/lack of cashflow/increased condo assessments/not there cup of teas for business). 

Buying out-of-state is an option, but through research and risk assessment are crucial.