As I was preparing my taxes, my tax professional advised me that management LLC is redundancy and it doesn't make sense to have, it's like moving my money from one pocket to the other.

You should leverage the paid off property that you have by doing a cash out refinance and then use that to buy a new build for $300-350k putting at least 25-30% down, you can find these that will rent for 7% (annual) of the purchase price and have very low property taxes and insurance.

Current expenses are $1300 per month (water, sewer/septic, taxes (property and 10 homes) and insurance (liability and homes).   

Some things to consider are: if minor maintenance is included, if they file the occupancy tax on the owners behalf, if they hire the cleaning service and if they "eat" the credit card fees or pass them onto the owner.

However, like other tax rules each situation is unique to each individual and there are regulations that must be followed for the deduction to be applicable.What is an Investment Interest Expense?

"Just try NOT paying your property taxes, you'll find out real fast who really owns your property".

I know it is logical to think you could deduct half of the shared common space, but unfortunately the tax law wasn't written to allow that.  

At this point just making connections and adding value to relationship building through the the expertise I have, 15 years in MA and VT. 

Begin with lesser initiatives to obtain expertise and build a track record, then progressively scale them up.

Hello tax experts, I have specific question on filing taxes for Short term rental property (30 days or less).