Cash flow has been hampered by an increase in cost of ownership recently, specifically insurance. 

Are you cash flowing the property?

This would allow for a longer carry back with up front cash flow.

That looks pretty bad for your cash flow.

There are a bunch of different figures associated with this decision, such as new interest rate, old interest rate, cash flow of new property etc, but I'm having a hard time getting my mind around how to analyze the decision mathematically.  

Because cashing out properties now takes 12 months on title, brrrring has gotten a lot slower for me.

He is great with investors and can find deals that cash flow much easier, including some off market stuff.

I can pay for all my problems using the cash flow from my current rentals.

- If so, 1031 into something bigger and easier to manage and then when you pass, the inheritor receives your property(s) at a stepped up basis - subject to Inheritance Tax limits.Otherwise, sell one every 1-5 years when you need the cash, so you can plan expenses to offset capital gains.

The modest cash flow could be reinvested, eventually allowing me to build a portfolio of income-generating properties.I recognize your point about needing $2.5M–$3M in cash to consistently replace a six-figure income.