As the new owner, you’ll want the lease and your landlord insurance policy to take effect as soon as you take title to the property.Temporary Lease Considerations:While short-term leases can work well, leasing to a seller long-term often leads to complications.

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

For instance, cities like Chicago are known for landlord-tenant laws that skew heavily in favor of tenants, and that risk should be baked into your underwriting.What’s your take on balancing short-term cash flow with long-term equity growth?

It very well could become a large enough investment to be worthwhile, also solving for "unexpected emergencies ", for the most part and would an easy self management situation if you were to live onsite in one of your connected townhomes.

I have some rentals up and down the Fox River as well.

If it comes down to it, might as well.

I also suggest you post your listing to "Short Term Rental Listing Advice" on Facebook and let them give you more feedback as well.  

I also invest in other assets such as stocks, and private companies as well.

It’s actually working really well and has been very helpful.

And while short-term rentals are the big draw here, there’s also growing demand for mid-term rentals from snowbirds and traveling professionals, as well as long-term housing for the increasing number of permanent residents.Yes, higher interest rates are a factor, but the strong rental demand in the Panhandle often helps offset those costs.