I’m interested in learning all about RE investing for cash flow and to have freedom of time, location and have a cash flow of 5k/mth from RE investment. 

Property 2 is 148k 2bed/2bath in an area I'm not familiar with but by the location I can see its 3-5 mins away from a college, hospital, and highways. 30-45 min drive to the beach.

Physical location doesn’t matter much, but having experience flipping houses in Florida is a definitely plus. 

The location of this property is north of Huntsville.

This could help secure funding and expertise in building and managing affordable housing.4.Explore alternative construction methods: As you mentioned, modular homes could be a cost-effective option for building additional units on the property.

Should they all be located in Florida or Massachusetts?

Seller financing is an option or locating a landlord who's exiting the program is another option just to name a few.  

You want a desirable location plus with minimal sloping/grading issues and minimal trees.

There are many tax providers you can locate on this forum to help you out.

. $34k could be cheap depending on assets, values and location