I immediately looked at the portfolio and raised some rents I had been putting off doing which was a start in a better direction but not an actual solution.

(How to deal with existing mortgage during the gifting process... prefer mortgage gets paid off, rather than become part of the gift.)Much thanks

You could ask your accountant about options for bonus depreciation or possibly updating the properties in order to receive depreciation deductions or write-offs for repairs, maintenance, etc.

You would literally be better off selling and buying an identical home in the neighborhood raising your cost basis.

One quick question...how important is off street parking to guests?

Good news is rates are starting to trend down and property values are still growing.The cash out can serve two puposes it can help pay off some high interest credit cards and be used for a down payment. 

Thanks, after research, it looks like FNMA keeps the mortgages in something called an MBS trust, then writes securities off those trusts.

For small spaces, you can't get a small enough (in terms of BTU) multi-zone unit and what happens is one unit receives refrigerant even when not running if the other is running, which due to the cold of the evap coil causes it to condensate and ultimately causes constant problems with drainage.Also, look for a mini-split where you can connect an external thermostat and configure the head unit to shut off when the set point is reached.

I do recommend house hacking to those just starting off real estate investing. 

You are asking way too much to start off with to get all four of those, but it is possible.