In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

All the regulators have become useless pawns.

A mentor should have practical experience and proven success.

Reach out anytime agreed. i am unfamiliar with his markets but $220 does seem very low. a sf room mate/ BRRRR strategy seems more practical

I’m not sure all of the regulations/rules to this in PA though.

The combination of Germany's stable economy, well-regulated property market, relatively low interest rates, and the opportunity for long-term capital appreciation make it a compelling choice for U.S.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

Once you hit a certain number of loans (check with your state dept of banking and finance or dept of business regulation), they might require you to have a license.