For the property I purchase, I’d like to keep my monthly mortgage payments at $2,000 or less.I prefer a turn-key property since this is my first rental, and I want to start generating monthly cash flow immediately without the delay of repairs or managing two mortgages.

I have equity in my CO rental; I don’t have a large enough sum saved up for a down payment yet so I’m wondering if a HELOC would be an option on my CO property. 

Use the 20K as a down payment on the next house hack and don't touch your current properties equity.

If you are going to be an owner-occupant, want a low down payment, and are planning to do a renovation, the FHA 203k and Fannie May Homestyle loans are your best optionsHow do you know the property is currently upside down on the mortgage? 

I had a heart-to-heart with the contractor and made it clear what our expectations were and no more money (he was asking for a second payment of a three payment contract) would come his way. 

This would be an opportunity to discuss deferred payments and a 5 year balloon. 

On the lease, he'll pay me $100/m over my HELOC payment and all other expenses, including the refi cost, inspections, title work, etc... 

Since you'll be owner-occupying, take advantage of low down payment loans like FHA (3.5%), Conventional (5%), VA (0%), or a 203k loan for renovations.

Based on the CU's loan calculator, we can finance that over 60 months for a $320 payment. 

When revenue is low in the first couple of year, so is the interest payment.