If it sold for $120K in 2007  , and your rent is $2000 a month , the landlord is probably cash flowing rather well .   

House hack another property with a low down payment loan and use the remainder or the proceeds to either renovate or purchase another investment property?  

Personally If you like your current residence and hope to stay there long term I would forgo major improvements on my primary and use all investment savings to make you more money and cash flow. 

Yet the payment processor is issuing the 1099-K to the property management company.

My dilemma has been that I've gotten a little behind on some revolving debt that selling this property now could eliminate in addition to giving me cash on hand to trade into some better value or start a new construction duplex project I've been wanting to start.

It’s a great way to grow faster.HELOC or Equity Tapping: If you have equity in another property, using a HELOC or cash-out refinance could help cover the down payment without affecting your DTI as much.Seller Financing or Creative Deals: Look for sellers willing to finance directly, which bypasses traditional mortgage qualification hurdles.Scaling quickly often involves combining strategies—play around with what works best for your goals.

I purchased both as a package and for the next six years enjoyed great cash flow as I paid the tax on the house lot annually at about half of what it should have been and neglected to pay anything on the tennis court lot.  

So either you pay for the repair out of the idle cash in your account, file an insurance claim and use those funds, or rollover/transfer funds from another retirement account to cover the cost. 

They have had 100% occupancy at market rates and currently bring in around $2,000 per month in cash flow.

For the couple hundred in extra 'cash flow' you get by doubling a payment's term, I'd much rather be done with it sooner.