For Middletown Ct that is quite a market value increase year over year.

I've looked at Box and I don't mind paying for cloud storage (since otherwise you pay with privacy) but at the time I didn't like the application integration on iOS as much.

The preexisting rental agreement is way under market value for a 2/2 at 917 Sq ft.

Quote from @Jonathan Dempsey: 10 Best Pocono HOAs for STRIntroduction to the PoconosThe Pocono market has long been a popular vacation rental market due to the area's many natural attractions and the region's proximity to major metros Philadelphia and New York City.

When the time comes, if Texas is too far or expensive - don't forget about the Scranton market - that's a hot spot where a ton of NJ / NY residents to start buying affordable rentals. 

For example, I could get $1,500 as an LTR without paying utilities.

I'm looking for guidance specific to financing my first property and what market I should do it in.

She’s been paying rent but we are not renewing with her.

Two out of the four have been renovated and are currently rented.House 1: Before purchase the tenant was paying $900/month.

I wouldn't pay a dime.