I came here in early 2022 and bought my first duplex in Forest Park, IL and was able to effectively house hack.

It could be heat in the winter(in Michigan) or AC in the summer (imagine them running AC at 70 degrees all summer in Phoenix) or just general disregard for leaving lights on and things like that.

Dead winter is not an ideal time to rent out a property so I expect it could take me 4-6 weeks or require discounting.

We've had luck in areas or zip codes like 32210, 32208 (Harbor View, Lake Forest Hills) and 32211 (Arlington).

Quote from @Marc Winter: Based on the last 4 housing crashes I've survived (and lived to talk about), we are teetering on the brink of a major downturn in many geographic areas.  

Haven't seen activity increase like crazy but I think end of August(after school starts) activity will increase before the Winter

In Pinehurst NC, known for golf and the US Open, we do have some STR that are often medium term...during the winter months when golf is not as enjoyable, we get medium term renters. 

@Bryan Galaz you can start by getting a HELOC (Farmers and Merchants Bank, Lake Forest) to see how much you can borrow. 

On the other hand, the tenant may be more likely to move to a different apartment since there are more options on the market and they could find a better fit.I think you can make an argument that it's actually better to have leases expire in "slower" or less desirable moving seasons like the fall and winter.

For example crank the heat up to 85 degrees and open all the windows in winter causing a $1,000 heating bill for the month!