But if I do ok - -it's a nice enhancement to ROI.

You ask very good questions & it is clear that you are trying to do your due diligence thoroughly, and I commend you for that.The term "Fountain Square", the neighborhood & its boundaries, are often used quite loosely, sometimes because of lack of knowledge (and with no bad intent), and sometimes, for other reasons (enhanced marketing of properties).Below is a link to Downtown Indy, a very good resource & professional website.  

I will be years trying to recoup the investment but it enhances the building overall and will keep tenants happier I guess.

I usually provide a small 2-3 page example of a straight sale versus a vendor carry and offer to have them visit my (or another) accountant for an hour on my dime.You first need to educate yourself, so you can spot when a Vendor carry could enhance a vendor's situation.

But if you're primarily working with excel and looking for fairly basic visualizations, you'd be surprised what you can do with Excel power pivot and power view; there have been some recent mapping enhancements made.

Those of us in the IT / tech sector know about many ways that we can enhance the value of properties.

With a DSCR, I’d be able to find a cheap property i could enhance with my own funds and skills to make profitable, and a DSCR would allow me to do that solely based on what I will make once it’s rented? 

I have experience building something very similar so can certainly provide insight and logic that can be used to enhance it from investor point of view.

Therefore, they received no reimbursement or anything when they moved out.We do try our best to help T/Bs understand that their money is always best spent getting themselves qualified to buy first, and then on enhancing the home.

Not sure how much AI they were using, but certainly some kind of predictive models.I think there is probably some room for technology improvements and AI enhancements.