@Ryan Copeland I personally love pricelabs.

@Ryan Tierney It sounds like you have the start of a great plan.

to me this becomes a very personal choice where you have to weight your Options.IE your own personal financial situation .. 

@Ryan Hemeyer looks like you are an agent...I know your MLS has some good tools...RPR and Realist (core logic) should be your first stop...if using RPR, just make sure the Commercial switch is toggled...

My name is Ryan and like all of you, I'm interested to begin my journey in real estate investing.

I'm not super familiar with this area in Illinois but I'll include a zone map to help you find some quick fixes- just figure out he zone specifically and go with a zone appropriate choice(s). 

@Stephen FooteHi Stephen- yes as far as going with 20% down and that eating away at cash reserves the best choice then would be to wait until you can go it alone.

You had no choice. 

So in the future you could refinance the rental to take out tax free money to pay down your primary residence to accelerate this even more, or sell the rental to capture the equity in it to pay down the primary residence.Regardless of your choice- refinancing would probably be in your best interest on one or both of the properties. 

@Kevin LeAt some point it becomes a personal choice in terms of which area works best for you (SF/South/East Bay/Peninsula) etc.