@John PerezWelcome to the site.Your going to need to reduce your debts and increase your earnings.To buy real estate you need at least 1 or 2 the following.CreditMoneyExperienceAt the moment you don't have any but that is ok.

If my newly formed LLC purchases the properties from me at the same price I paid for the properties within the past 18 months I would reduce my transfer taxes by thousands.

I would suggest the Seller that they reduce the price to the open market to $200K and get a Buyer who is willing to pay it, and potentially start a bidding war.  

I believe real estate is about calculated risk that is reduced by increased equity.

He was able to reduce it by greater than 49%-63% of what I started out with.  

It reduces your personal risk in the deal.

Granted, rent would go up over the course of 10 years but I imagine the interest on the HELOC would also.So how can I repay a HELOC and not reduce my cash flow down to $140 bucks?

I have a whole post about it.https://www.biggerpockets.com/forums/61/topics/364937-reducing-flood-insurance-costs?

Fyi they did reduce the rate from 12% to 5.75 on the mod

But you also say you have reduced the price twice.