When I had an issue arise during the closing process, I was able to turn to my investment counselor (Steve Olson) for input.

So many problems arise out of the fact that the units are being used for totally different purposes.

The showing is scheduled and as long as no big concern arises, I am going to make an offer.

Question - if a second vacation home is rented on STR basis after closing, what issues could arise when the insurance policy is changed from homeowner's to STR? 

There is not much investigation needed when a tenant has a judgment arising from a lease, they lose.

The old adage is that you "marry the property, but date the rate" meaning that you can refinance down the road to lower the rate if the opportunity arises.

Hopefully, if that situation arises, the notice results in attitude correction and the lease can continue uninterrupted.Having said that, if the eviction is 5 years ago, I'd probably accept the couple - but let them know I'll be keeping them on a short leash.

The Exclusions From Coverage for a standard ALTA Owner's Title Policy provides:The following matters are excluded from the coverage of this policy, and the Company will not pay loss or damage, costs, attorneys’ fees, or expenses that arise by reason of:4.

However, under the "Disparate Impact" legal theory, fair housing issues arise when denying persons with a criminal record involving non-serious offenses and offenses that are remote in time. 

Most of what I shared are proactive measures you can take to greatly reduce your liability exposure and shield you from a host of claims that commonly arise in real estate.