If the property does not sell soon after the rehab is complete, we will rent it out so that we have supplemental income to cover the cost of the loans from the hard money lender and the original seller.

A 506(c) raise would enable you to generally solicit for investors as long as you "reasonably verify" they're accredited.  

The series LLC structure enables you to house multiple properties in one LLC but not risk all units if a lawsuit were to occur.

Yes, accelerated depreciation available in the early 80's enabled me to live rent free when I bought and lived in one unit of my triplex.As to going thru gyrations renting from your LLC, why have deductions for one entity and income for another?

You can report that to the insurance co, too, and hopefully get a supplement.  

Hello all,I am a homeowner looking to supplement my income by purchasing a second home, preferably a duplex, and renting it out.

In answering your ‘supplemental’ question...

Do what you have to do now to not only make their life easier down the road but also to enable you to obtain the lowest rates and best terms possible for yourself. 

Technology has enabled communication with a remote CPA through phone calls, emails, skype etc.

I would probably bet that you can never stop learning about this massive subject, however i would like some good old fashioned books to flip through to supplement my education.