Am I comfortable managing a property?

However, if your tenants aren’t comfortable with the system of suddenly have a new method of spending their money (debit card) you may find they spend the rent money before paying you!

We are thinking of asking $2100, but will still be able to contribute to the maintenance/vacancy account comfortably if we come down to the $1800 range.

I also have more capital to invest than my potential partner, and would be more comfortable investing in a larger property (and thereby more sense to use a property manager, but that's a different story). 

The first floor is reconstructed into a salon and the second and third floor are now a comfortable Loft style townhome.

That would have put me into an area where I wouldn't feel comfortable and I'd be trading the short term stress of 'shoulda could woulda' with the long term stress of 'am I gonna be able to make money on this?'

Cute, Clean, Comfortable are the best practices.

Is dry and comfortable.

I'd try to take the time to understand what this property would look like if the numbers come in at a worst case scenario, or at least a worse scenario than what you predict, and see if you are still comfortable with it.  

Not sure if that's why they were gated or not, but the homes were noticeably cheaper...I'm more comfortable investing in a community that has a lot of STR's.