Just track everything you do in an excel spreadsheet or google sheet.

Reaching out to property management is an excellent idea - we love and trust the company we use for our rentals, I imagine they'll have a few suggestions.

First, a PMC has no ownership in a property, so once you factor in appreciation and equity, owners should make far more than a PMC.2nd, every owner thinks that PMC's charge too much, yet they expect excellent service!

@Nathan G. outlined an excellent system for what the process should look like.

Typically I can export the transactions per month into Excel and it's not more than 30-40 rows.  

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.