I am scared of servicing two mortgages in the case of a vacancy.

Self storage based on aself service model can be done while your golfing, out fishing, ortraveling.

If you are trying to come up with a way to finagle the occupancy requirements while using an amazing loan (that you earned based on your service) like a VA, I would say you are starting off on the wrong foot.

Additionally, transitioning certain activities, such as maintenance and repairs, to be conducted directly through the business entity could strengthen your position for claiming deductions.

.- It's impossible, given the daily little decisions that have to be made dealing with tenants, maintenance, paperwork, cities, etc.So, how much control are you really willing to give up?

It’s also important to be as specific as possible in the scope of work for each line item—clear details can save you from misunderstandings or unexpected costs later on.I specialize in consulting services for situations just like this, helping clients work confidently with contractors by bridging the knowledge gap.

And the condo debacle in FL will be churning for quite a while as these rogue HOAs try to get realistic with deferred maintenance, new requirements, and freedom for people to use as they need to afford them.One thing to consider would be to 1031 all of them in a consolidation exchange. 

Her unit needs to be improved or I fear that the costs to fis it up will grow without decent maintenance.

If you are going to outsource management you will get everything done for you, but you will have some of your cash flow used for services. 

Compare this to your total monthly costs, including mortgage, insurance, taxes, vacancy and maintenance.