This way your net mortgage expense is somewhere between dramatically reduced and eliminated.

It'll certainly eliminate most - if not all - owner occupant buyers regardless of price or other considerations.I wouldn't be thrilled to buy a SFH investment property with that lease in place either unless it was such a screaming deal that I could afford to take the negative cash flow hit every month until the lease was up and then I could cash out.

Change of anything from bankers management, shareholders, economic concerns, etc. can change their intent and go for the Due on Sale.I believe the question should be: "How can a deed transfer be done, if at all,  into a Series LLC if the property has a loan that is not in the name of the Series LLC to minimize or eliminate the Due on Sale clause?"

If you over pay, even if it cash flows, then you have eliminated one of your exit strategies and painted yourself into a corner.

Im thirty one years old so I was looking at just trying to eliminate debt asap!

Which is not too bad as long as you save enough to have a couple months with one vacant unit.You may also want to consider putting your "rent" into an account to save enough money to refinance with 20% down to eliminate PMI.

This way you eliminate paying interest and bank fees etc.. until you need it to purchase another investment. 

IF I were you I would concentrate on the debt first to eliminate potential financial problems in the event you hit the inevitable rough patch should you decide to move forward on the rental. 

Other than the usual advice of finding the right tenant the most useful tip I can give you is to eliminate/minimize variable expenses.

This can significantly eliminate some of the issues with trying to coordinate several sales into one purchase.However, there's a couple more serious issues you may have.