A better way to split this up is to look at tax assessor data.  

I am thinking it would be Essentials because then you can pay bills online, but if your bank has that feature and you can just have all your bank entries downloaded, I am not sure if that is necessary.  

seems like it pulls data from zillow

To answer your questions It doesn't matter what kind of software you are coming from they are going to tell you to export your data and fit it in to their google spreadsheet.  

While the data is excellent and affordable, it isn't intended to be the only tool in your tool chest.

I'm slowly researching that now, but unless I want to get a Thai wife (and I kinda like my current one) there are a lot of barriers to entry.  

The legal proceeding is called a Forcible Entry and Detainer action. 

I have a methodology that has helped me cash flow on all my properties since my first property acquisition (85k property, aquired for 67k, total closing costs 950.00)Before making an offer on a property put it's address in www.rentometer.com to get the market rents, cross reference that info with a conversation with a highly successful area realtor and let that data guide your purchase decisions and you will always cash flow.

I entered into IT right around 2000 where anyone with an IT degree was making 70K+ during college that entry level wage dropped to 30K.

You should be able to generate similar data for all the cities you are considering in an evening.At this point you are probably down to two or three cities.