Hey @Forest Wu, you indeed need to own the property to claim bonus depreciation on it. 

Heating costs go up in winter, as does electricity due to the reduced natural light and more people indoors.

We still see deals in Forest Park, Elmwood Park, and other surrounding burbs from time to time. 

I'm looking for the place that everyone wants to stay and is able to attract both summer, and winter tennents. 

Yes, it will affect things like roof longevity and could add things like snow removal in the winter, so you need to account for that.

We typically fill leases for our SF in a week or two, even in the winter. 

I have visited the area for 4 winters now for a long weekend in February to visit my in laws. 

With different rental approaches such as Mid-term (or month to month), we also frequently adjust and re-evaluate pricing in the off-season or winter months as needed in order to get a unit filled and avoid long-standing vacancies.Depending on your focused market, I can recommend a solid investor-focused lender that may be a good fit to strategize on how to get you into your next property. 

However during the winter or at night when there’s more likely to be deer and moose out it complicates things.

Heating costs go up in winter, as does electricity due to the reduced natural light and more people indoors.