I put my money where it’s going to perform best, either in real estate or my brokerage account in the form of an S&P 500 index fund.

@Johnny SmithThere are other ways to reduce your taxes besides real estate.I recommend finding a tax strategist who specializes in real estate taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Does anyone have any good recommendations on books or accounts I can follow or read to learn more? 

This PM will be trusted with the accounting, collection, and transfer, of tens of thousands of your dollars, or more.

You can open a business bank account, sign contracts, and handle expenses under the company’s name, keeping everything clean and organized.

I am planning to include the estimated property value and the funds that will be transferred into the business bank accounts.

You can basic info on short term rental projections and occupancy rates with a free account, but will have to purchase a membership to get detailed info. 

The 150k is what's leftover after 30k/30k put aside for our personal and property emergency accounts.

I'd be letting my tenant know that their goverment is failing them.Actually, the HAP contract does say that we can charge the HA a late fee after the first two months of occupancy if reasonable and otherwise accounted for in the lease.

One thing Airbnb and VRBO can not do is help schedule cleaning and maintenance tasks, owner accounting reports, and direct booking options that hosts need to go to next level.