We don't have any issue getting it booked up for the season.

Being fairly new to land lording I felt the need to gather a bit more insight from other seasoned professional with how to proceed, but you're absolutely right. 

Work with a seasoned STR realtor or STR PM to give you more options of a win win deal

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Seems like a good option is STR during peak season and MTR in other times of year.

HEY BIGGER POCKETS FAM HOPE ALL IS WELL SENDING LOVE AND PROSPERITY THIS HOLIDAY SEASON TO EVERYONE !

As a result, competing against seasoned investors in the multifamily space can be challenging, especially for newcomers or those with less capital to deploy.On the other hand, single-family homes (SFH) are typically the go-to choice for primary homebuyers, who are not always as cash-rich as investors but can still secure financing through conventional loans.

Again, if you feel like selling it you'll be in a good position to do so in the upcoming months(Spring-Summer season).

@Kevin Zmick the rental market in Chicago can be very, very seasonal.

Whether you're a new or seasoned investor, feel free to reach out.