Hey @Robert Cucino, you should just buy what you want and move ahead.Nothing we say is going to deter you obviously.Just hit up AirBNB and VRBO and see what others are charging, occupancy and amenities, then get it.Good luck with your project!

While condos might be all someone can afford to owner occupy or invest in enter at your own risk and if they are talking about future special assessments you will likely scare future buying prospects away. 

What is the current prospect of you finding another job?

(This, of course, depends on one's assumptions about future appreciation; the prospects of which I have my doubts.)

We’ve published blogs and courses on this topic for a few years but unfortunately we still see the incorrect application of law on 70% of incoming STR prospects!

For prospects seeking to rent many months in advance we are typically declining those and seeking to lease up as close as possible to the next available date so as to prevent potential gap periods that will be harder to lease. 

Quote from @Casi Rice: @Jason Wray your prospective is greatly appreciated!

Granted it is unlikely to result in a home run, but it also is less likely to fail big and negatively affect prospects for years. 

And most investors don't want to hear this but you have to pay for a feasibility review even though this is just a prospective property.

I'm originally from Western PA as well (Slippery Rock) and now reside in Atlanta.Here is how I am looking at it along with the assumptions I am making:1) I think the growth prospects are better in the Atlanta market than Pittsburgh from a pure demographics standpoint.2) I estimate your return on equity at 7.2% currently3) Over the long haul appreciation is going to take you further when it comes to net worth than cashflow will4) Doubling of the roofs is doubling the expensesThings to consider:1) What is the year built of your Atlanta property vs. what you could replace it with in PGH?