When the housing market became seller friendly, I unloaded 5/6 of our long term rental units, paid off our house with that and invested in stocks and mutual funds…completely no fun, right??

@Pixel Rogue everyone has different future plans - many though haven't thought that far ahead!

I think this is a calculation a lot of homeowners are making right now--especially if they have a low interest mortgage, equity, and their house will cashflow as a rental.The choice is a personal one of course, but I think your future self will thank you if you pull out some equity from your existing home with a HELOC for the downpayment on the next house and a cushion renting your current home, use a property manager as you have other things to do, and buy the next house and do the same thing again.

I'd be heavily focused on mitigating that future tax liabilty rather than directly supplementing that income.

***************************************************************Ah, so much for betting on Future Appreciation. 

just like stock brokers in the day !!!

Real estate is not the stock market and it's called buy & hold and not buy & sell for a reason.I did sell a few properties about 10 years ago when I learned the hard way that going into cheaper neighborhoods was not the right strategy for me, so that was basically a strategy correction and it was necessary, but also costly both in terms of dollars and time.

It is something I am interested in doing in the future, potentially even this year, but I am curious how to put concrete numbers to this decision.  

the only thing with that is protecting future landlords.. but then again thats a personal choice..  

There still is a lot left to do, but I believe I am adding a ton of value for the future.