@Matthew Burns Elenis is abolutley right, starting at your age you are going to be serious Pro in 10 years.  

You can buy a home in the areas you mentioned that needs rehab work in which you can add value. 

I suppose I should've mentioned my "why" factor.

Someone mentioned the 1% rule, however if other expenses such as property taxes or maintenance are large, it might still not cash flow.Every deal needs to be analyzed in its own right to see if you're comfortable with the risk/return.  

Can you mention all together the things you would tweak in the process or do differently now that you can look back on it?

I recently spoke with the owner of a property who is very interested in selling. he mentioned that the property has severe foundation problems.

My realtor mentioned that once they clear that number the leftover money may go back into my principal but he wasn’t sure and my loan originator told me she was also unsure but she did say that banks can’t profit from a short sale.

I notice you didn't mention the money owe me on the other property, which is a totally separate agreement.

If these features in your unit pale in comparison (age, condition, etc.) to the others, it puts you at a competitive disadvantage. 

David Greene's Long distance investing book goes over many of the talking points that you just mentioned.