@Peter Mckernan @Mark Frattini@Allen Tracy @Katie L. also looking for a RE-savvy CPA in California who can work with me to execute the STR strategy to offset W2 income with losses from a cost seg study I'm conducting.

Even though I don't think there's a way to get out of this without taking some sort of loss.    

Each of them had $20,000 of unused "suspended" losses from prior years plus $5,000 of current year losses.

If I go with the 5900 policy I will be operating at a loss and I will be forced to sell the house. 

Also, you are buying property at a loss from Mom.

The only thing I would anticipate needing in terms of capital expenses in the next few years would be a new HVAC unit which is on the older side, but we have already budgeted for that and have a service contract with a company that manages our HVAC, water heater and oil tank.Am I crazy for thinking that a property management company would be an unnecessary expense in my case?

I've gotten Proper insurance in Palm Bay for building, liability, loss of income, etc. for around $2800 WITHOUT wind and paired that with a wind-only policy for also around $2500.

You may have current or prior years losses that would offset some of your capital gains.

Over charging on repairs can be the difference between profit and loss for a lot of smaller landlords.

Just got an email that they want us to put in another 26% of our invested capital or it is going to be sold at a loss.