Also besides residential there is commercial and industrial lands and a host of zoning issues.Each aspect and real estate type has maybe similar, but largely different skill set requirements. 

Post Part-Time Job Posting on Indeed: I have posted part-time jobs on Indeed (or other job posting sites) for specific jobs and got a list of reliable workers looking for part-time work.

Your goals should follow the SMART criteria: specific, measurable, attainable, relevant, and time-bound.

It's very non-specific.  

To combat this problem, a great management company who will have your back and navigate the ebb and flow of the ever changing climate of these rental sites is essential.Regardless of industry, when one or two of the providers consolidate power and foreclose all competition, this type of behavior inevitably follows. 

Federal Regulators HATE smaller real estate investors for some reason and really come down hard on banks for funding their deals.

Compare a few direct booking websites/tools and you'll see that most are exactly the same: simple, templated sites with a front-page search/map, property-specific listing pages, and integration with a payment processor, like Stripe.

Happy to answer any specific questions you have.

Specifically, I'm interested in finding a lender that allows a 10% down payment on investment properties.If anyone here has experience investing in these areas or has any lender recommendations, I'd greatly appreciate your insights.

Hey @Seth Hunt there are lots of Wholesalers on here but might get better connecting in one of the wholesaler FB groups specific to Chicago.