Low % down would be ideal, but total rents just don't cover PITI once I move out with current rates and home prices in the area.

The benefit of having a software is the ability for tenants to pay rent online, submit work orders, sign leases electronically, and the ability to complete end of year owner taxes. 

Quote from @Alex Breshears: Quote from @James Blair: I totally agree.

If you're coming from a traditional rental, managing a STR is totally different. 

I found much greater success cultivating relationships with my local brokers/agents and consistently reviewing material online. 

Maybe get it on more sites.Wix: Offers total control over website design, 500 MB of storage and bandwidth, free website templates, and access to the App Market.

I have a six-figure W2, and I receive stocks gifted to me and bonuses totaling upwards of an additional six figures a year.

You can monitor them online, or even better do some mystery shopping.

To get started, you can do the following steps:Participate in online communities and real estate investment sites like BiggerPockets.

Increased property taxes may have an effect on your total investment returns and cash flow.Make Connections with Local Investors: Gaining knowledge of the Chicago market may be achieved by establishing connections with real estate brokers, property managers, and other experts in the field.