Just remember this would not be viable in the winter. 

I'm wondering how much of an impact there will be if I let them stay a few extra months, and then I'm potentially stuck with listing it in the winter or some other inconvenient time?

Came back to my apartment after Winter break and noticed some cups I had left with water in them had evaporated and left behind an oily/heavy metal looking residue.

You are aware that the walkways, sidewalks, steps, driveways, and parking lots may be slippery especially during winter months based on weather conditions.

Fewer, however, said their household income is significantly higher than it was a year ago.With the housing market now in its historically slow winter season, some agents are reporting activity is “frozen.”

This is not to say you should not invest in that area, just have a back up plan e.g. winter rental or long term rentals while you wait for a license to become available. 

In a seasonal market like WI where things slow in the winter, there is also risk of holding a property longer than anticipated. 

I just flipped a house in st cloud last winter.

We are looking to take advantage of the WFH-friendly environment Covid-19 has created and spend the upcoming winter down south.

It looks nice, but it is a ways away from the I-5 corridor and a long drive from Spokane.It doesn't look easily accessible in the winter for the most part.