Is it a requirement to pay off all collection accounts or charge offs from years ago to get approved for a mortgage.

Since your goal is ultimately cash flow, the best way is more than likely going to be somewhere out of state where you can make the 1% rule work and collect rents each month.

With this hand we were dealt, we collectively knew that we couldn’t move forward any further.

(This could be doing real estate closings, evictions, collections, creating notes, doing entity work like operating agreements for LLCs, etc)Are there areas of real estate law that you try to avoid?

So if the tenant did that, the landlord would not be “retaliating” by attempting to collect the past due rent or terminating their tenancy if they didn’t pay it in full, he’d be doing what the law allows him to do and I’d assume what most any landlord would do to enforce their rental agreement. 

I collect 1st month rent and a security deposit that is roughly the same as first months rent. 

If it's in the low rent areas, and the damages go beyond the security deposit, you most likely won't have much luck collecting on the balance and have to write it off as a business expense. 

Would like to refund myself the $50k with low interest rate HELOC and collect the spread between the land contract payment and my HELOC payment.

If yes, do you have a long-term tenant in place and for how long have you been collecting rent?

It's just like Landlords that complain about bad tenants but never take ownership of their screening process (or lack thereof).A lot of property managers are amateurs that sucked at sales and decided to collect rent for an "easy" paycheck.