But this condo is on my current street, so I know what it can command in rent, which is probably 1,000-1,200 as it is a 2BD/1.5 bath. 

Not the nicest of neighborhoods, but they still command a hefty rental price.Then again, since this would be my first property, Pennsylvania is attractive as well, because although the cashflow will be lower, I'd likely be spending under $100k.

The home currently has bookings several months out, including during some big local events that command high prices.

But will getting rid of the garages make it harder to rent or command a lower rent than you're anticipating?

@Shekar Kollu it all depends, start to look around the area you live and see how that city rentals are priced , what kind of rents it commands and there are bunch of spreadsheets in biggerpockets you can plug the info into and see how it does as a rental and once you are comfortable with that area you can start moving to different parts of town.

The owner can often command a higher monthly payment under these terms than they could in a rental arrangement.Watch Out!"

He said that it doesn’t command higher rent and that in the Greenville market people want to bring their own.

Daily rentals have a lot more management overhead and therefore command higher management fees.  

Can you command any more for section 8 in your area?

Or maybe they did the light rehab in 2014 and $845 is all it commands.