I do not wish to keep the current tenants and was hoping to learn the best way to handle the situation and give them proper notice.

I will just have to learn how to balance that with hiring contractors to keep the ball moving quickly

I choose to jot-it down on a notebook where I keep track of my expenses. 

However, he (you) should keep it "clean" and not also use it for personal reasons.

I'm trying to evaluate if we should keep the property or sell it/1031 exchange into another investment, but I'm struggling to figure out how to do the analysis.Initial Purchase: $65,000 (Cash)Estimated market value: $250-270k - We'd clear $200-250k if we sold.Current Rental Income (after expenses): ~$1,417My gut tells me that we can leverage the proceeds into higher cash flowing investments, but I don't know how to do the math.

But now he is staying so we decided to play the cat card, and told him that per his lease pets not allowed and if he would like to keep it we will need to amend his lease to include additional $100 pet rent plus collect additional security deposit.

-Most leasees never exercise so 3 to 5 years from now... you keep the option fee, and had the benefit of rent that was probably above the market rate for your area.The drawback is that you don't get the ~$250k(after selling expenses) to play with. 

I'm looking for a new lender for this HELOC product and I see this as the only solution if I'm going to keep my low-rate, first position mortgage intact.

Using a WY statutory trust for each property, they said we would be able to keep our anonymity and have a layer of protection that would not spill over to other properties.

Sometimes they keep rents low.