I will have a solid amount of working capital, and I'm looking to put my team together.

I'm also calculating 20% of the rent in capital expenditures and maintenance ($440 per month).I did run the rents through rentometer.com and the average is $950. 

So I'd take the hit on capital gains and be pretty happy about being free of one rental responsibility and the mortgage on my house.

Turnovers cost a lot.Last, inevitably there are capital items. 

And this assumes I own the property outright... or have the capital needed to pay it off.

I'm just trying to figure out the best way without needing a bunch of capital for cash purchase.

If you have lived in that home for at least 2 years of the last 5, you could sell and any profit might not be taxed as a capital gain.

It depends on the level of the broker and their network.I have thousands of commercial retail property owners built up over the 15 years in business nationally.

In these scenarios I am assuming a loan of 3.5%-5% down as I do not have the capital for a larger down payment in the expensive Chicago market.

Then if you had an emergency repair you needed to finance, at least you know that capital would be returned to you in the short term, and is earning a nice return, usually 8 to 12 percent.