We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

Repeat as desired.

I live in a very desirably town in upstate NY, refinanced at a super low rate, so will keep the house as a rental.

The neighborhoods are not upscale but they are desirable so good tenants are typically found quickly. 

If it's just a money grab and there is no desire to associate with the aforementioned, you will most likely be on the losing end and feel very negative about the program.

Nice to have a problem that the properties have appreciated so much that the LTV is below my desired LTV goal.  

There is a mortgage so that also adds to the amount desired, though my inexperienced self still feels it would sell for a pretty penny once fixed up.

I suspect maximizing the investment might make it slightly less desirable as an owner or at least the renovations might have lower ROI if sold to a homeowner.

I have no desire to be part of any lawsuit or liquidation event.

I also never had to worry about vacancies: if you own a desirable property, you will always have people lined up to rent from you.