Here's how the treatment of capital losses typically works:Netting Capital Gains and Losses in a Tax Year: In a given tax year, you first net your capital gains and losses.

Brandon Eleazer - the link works fine for me - just tried it from a different computer even.The BPL has two payment options; here is a verbatim statement from the page in the link:"The lifetime license fee is $300, made payable to the City of Philadelphia.

I see they suggest offering the tenants the option of paying by Credit Card.

I'm guessing it would be easiest for them to come two weeks before their move in date and get an Airbnb and tour different options and make a decision quickly like you said. 

Take a good look at your budget and explore different financing options, such as traditional loans, FHA loans, VA loans, and private financing.

You will be eliminating a tax break that can be hugely beneficial to you as you enter retirement.You're most financially beneficial option would be to sell those properties and do 1031 exchanges into other real estate that is passive in nature. 

What are other options to buy and hold while recycling my cash and not getting too deep on negative cash flow?

Either way, there are a number of good options currently on the market for the goals you have laid out.

I plan to self manage, but it's good knowing a middle tier management option between self managed and full property management - without a huge PITA factor :)

Rental income is typically subject to taxation, and you may need to report the rental income on your tax return.