There is so much risk for the seller in most cases it makes absolutely no sense in this market for them to take that on.#4. 

STR's probably take more effort than investors expect, but they are a proven and generally less available (due to regulation) asset class. - Do you data research.

What considerations should you take into account in fleshing out if it is a good deal or not?

I'd love to scale upwards to those mini-multifamily properties of 8-12 units, but I think taking some baby steps first will help learn and be better prepared for those larger scale properties. 

They teach their students enough to be dangerous but not enough to do deals on their own so the student 9/10 times brings the deal back to the "guru" to help close it taking most of your deal you worked your tail off for.

Thanks for taking the time to reply to my questions!

You can do the math, but assuming it takes 6 months to get your money back you will be floating these types of purchases with cash or hard money loans. 

If you take that into consideration, you are losing money on the property. 

Google earth and google street view is great but it doesn't show you real time dataIf I have someone offering on my listing and they are un represented and they do not want to be represented by the listing agent or a buyers agent I know for a fact that my client will get the better end of the deal in this real estate transaction. 

Take a look at the local market and see what some 2bd/1ba homes have sold for and what they would rent for.