Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: Best way to get that is by working with a real estate tax expert.

But education starts somewhere, and basic analysis and due diligence will enable the investor to avoid the worst investments.  

KS yoak basically made the situation worse.

Basically if there is no "living room" and there are no comparable properties with similar square footage and bed/bath count in your area the property becomes difficult to comp or sell and lenders will not be able to use it as collateral for a loan Excellent point.

This isn’t just about bookkeeping—it’s about setting yourself up for sustainable growth.Many investors use a basic system with at least five accounts: one for income, one for operating expenses, one for taxes, one for marketing, and one for reserves.

A concern, however, if we do a sale, is with the price, as I understand that if I sell at too low a price (say, $200K, give or take a few thousand to pay off my current mortgage), the IRS could assess a tax on my parents if the price is more than 25% below market value. 

We have basically switch some of our properties from short term Airbnb’s to mid term rentals.Currently looking to buy the next property to help accommodate some of the requests we are getting.Anyone else getting these type of requests for mid term stays?

Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: Best way to get that is by working with a real estate tax expert.

The Assessor's Office is doing an assessment on it to determine the new assessed value.

There are some lenders who specialize in lending for double closes and will basically send you the money for a couple days but I personally haven't done this and don't know what the charge.