My front end DTI is 26% and my back end would be 39% with the second mortgage. my credit score is around 710-760 depending on the reporting agency.

Most likely scenario is that you're able to add the improvements you're looking for and will be able to refinance into a whole-property mortgage in under a year, depending on the improvements.

I did a step up payment schedule for my business that I bought.

Of course, it depends on the facts here.

I just worked with an investor who had $5M in cash (he sold his tree-cutting business) and I was able to get him into 11 properties in AL and FL. 

It might not even be accepted on your initial terms and most states have buyer focused contingency periods, or a statutory period of 7-14 business days to remit the deposit, perform inspections, organize appraisals and generally renegotiate or cancel without risk to the buyers earnest money deposit.

If you want to shower me w/advice on my specific scenario:2x Duplexes4% Mortgage Rates / Very small loansMixture of LTR/MTR/STRActive Income (not very passive)Net Income around $24,000 in totality (however my books are a mess and am currently working with someone to CLEAN THEM UP so I can get a clearer picture)Would you a) hold; b) sell and open a franchise or other business venture ?

You can still easily achieve rates in the low 7s depending on LTV for a DSCR cash out refi.

If anyone has any good leads on businesses they recommend for the fence (temp fence with windscreen bc its Chicago, sandbags) and porta-potty, please feel free to share your sources.

It all depends on neighborhood and demand.