The other thought I have is that you will be unlikely to get current deductions in the future on rental losses.

Deduct these expense from the deposit prior to returning.  

(Or how does it work) When it's all said and done I pay $2,500 out of pocket for the work then I pay a $1,000 deductible  to my insurance that's $3,500 out of pocket to only have to wait for a check by my insurance company, this doesn't sound right to me 

Do I still qualify for the standard deduction? 

The Partnership would deduct the interest and you should have documentation of the LLC assuming the mortgage.PM me if you'd like that friend's information.You definitely need someone qualified, does not have to be a CPA, could be an Enrolled Agent or an attorney.

I would welcome comments, strategies, suggestions and introductions to tax professionals regarding VR property ownership, rehabs, deductions, liabilities, etc...Thank you!

So for a 100k home you would be looking at $310-890 annually depending on the deductible you were comfortable with.

I think NC stopped their state tax deduction, which is too bad.

I am pretty sure I take all the deductions I'm due and I've vehicles such as as solo 401K, self-directed IRA, Roth, etc. but I think I might be missing out on larger-picture strategies for investing and tax savings.

The return on your dead money plus the interest tax deduction far out weighs the 401K.