I understand this is a bit of a unique but I'm not trying to scam my family.

There are many brokers out there that specialize in the different niches such as Retail, Office, Medical, Land, Industrial and Multifamily (which is our specialty).I'd say the most important factor in selecting a firm to join is who will be your mentor. 

I think your problem is that USAA doesn't offer any products that account for the unique risks associated with bed and breakfast/ short term rental businesses.

That is a big issue here in Denver and in many other cities, but everywhere is unique. 

@Jake BaronThere is no "average" that an accountant will carry with them that will advise you saying your taxes will go up or down $$$ based on a certain income level.That answer is based on a wide range of scenario's.At the very least, you need to provide information such as budgeted income/expenses for the real estate property you plan to purchase, in addition you would only be including items related to the investment property.The portion of the property you plan to live in is considered personal.Downpayment is not necessarily deductibleThe cost of the building(not including land) is depreciated over 27.5 years(you can only do this for the investment portion).Closing costs are either immediately expensed or added to basis and depreciated over its useful life.Ohio is a unique state for tax purposes.

Hi, I have a unique situation and would appreciate some advice.

Alas my flying days are over though I have medical issues with balance and Vertigo.. hopefully can get my medical back..

I’m a medical sales rep during the day.

Additionally, vacation rentals offer a unique opportunity to help heal our beloved island as it is still recovering from the effects of Hurricane Maria (I go into more detail on this in my business plan).  

I have a unique situation I'm trying to find solutions for.