Can't say for sure what choice you should make except to say that you should try not to overthink it.

Join in on local seminars, networking events, and meetings for real estate to network with seasoned investors and gain insight from their experiences.Evaluate your options for Financing: Investigate your choices for financing multifamily residences, such as conventional loans, FHA loans, and other mortgage programs.

As for me I’ll bypass rules and evaluate each deal independently to see if it fits criteria I choice which I’ve chosen to provide the best shot at reaching my goals.  

I had no other choice since I couldn't find a lender to fund my rehab since they felt it was too small.  

This can be very expensive and is usually the worst choice because you can't justify the cost.2.

It makes much more financial sense for investors to invest where they make the highest return and then pay for a stay in the short-term rentals of their choice when they want to travel.

(Those which qualify of course) Looking forward to hearing helpful advice, things to avoid, what not to jump into, and learning ways of making the best choices for long term investing.  

Made poor choice in hiring first painter and the expense of labor and supplies - unable to complete job satisfactorily which will lead to a redo.

I would also make sure to know what type of financing you will be using--the traditional choice is a second home loan, but this doesn't allow you to use future rental income to qualify.

Letting your family use your property is your personal choice that has no profit motive, hence no tax benefits.