Alternatively, platforms like Twilio provide excellent customization but might require more technical setup for Podio.

@Sung Yu You can 1031 exchange your fourplex into a single-family home, provided it’s initially used as an investment property (rented for 1–2 years) to meet IRS requirements.

The area you're targeting might be too small for anyone to be able to provide any detailed insight.

There are best practices on certain items that provides a guidelines.Commissions are always negotiable like any other services, you can shop around for the best value for money.All depends on the risks that you are willing to take.

If you are the nicest 4/2 out there in the market and all the rest have not been remodeled in say 15 years, and your property was remodeled a month ago then the price on your property will be easily justified at a higher price on the listing side. 

However, we have a higher end market so it always struck me as strange that we'd only provide such a small amount since it doesn't cost that much more to provide more.

Quote from @Adam York: Contact your insurance provider and let them know you intend to rent out the home.

I'm meeting with a couple agents i was referred to through my network and am wondering what critical questions I should be asking them to understand if they are the right partners for me in this market, especially considering I will be managing this investment from the other side of the country, and what info I should be prepared to provide to them.

@Matt Smith - as @Christopher S. mentioned you cannot use an ADU unit in Chicago as an AirBNB as the city's intent with the program is to provide additional affordable housing. 

I provided a free rent back for 2 weeks so the seller could get her funds and relocate.