Selling could get you some cash on hand, while renting will help supplement your living cost.

Specifically, I am interested in the idea of supplementing my income as a software developer with income from note investing.

"This supplemental tax shall be referred to as the “CTA portion” of the Chicago Real Property Transfer Tax, and the $3.75 tax shall be referred to as the “City portion.”

I run a small business so my real estate investing is done more as a supplement than as an income.

It is a nice way to supplement that retirement check.   

There is a good podcast on BP that I heard that lays out a strategy of doing this once a year as a strategy as a supplement to your current income. 

Its a supplemental thing I do when evaluating a new tenant and I've found some good information on that site.Personally, get a property manager to handle it.

I think I can handle it, have it supplement my retirement, and keep building a portfolio in a controlled/steady manner to reduce risk and perhaps have enough holdings to switch careers for good!

I can send the complex through a private message.I supplement with Southern Resorts but still advertise on VRBO.

A checkbook IRA does sound like a hassle to set up, but I've been looking at switching my TSP over to a SD IRA to supplement my 401k.