I specialize in str Management And would be happy to go over your listing to help increase bookings.

Also have you talked to any property management companies to get their take?  

Given that he's got a long history in business but is struggling to cover $30k in Op-ex and marketing spend, my guess is that this is either not very well managed or is in distress.

Many DSCR products have requirements around rental management/investing experience and/or also that you own a primary residence.

I have a property that has been on the market for over three months now without receiving a qualified tenant and I may want to sell it to get some liquidity.It has also been hard to receive monthly profit for myself since my property management has a portfolio minimum of $2k until they allow me to take home proceeds at the end of the month.

I know for a couple of my STRs the management company uses the keypad system whereby they are able to set codes offsite for each renter and this is super helpful when working correctly.

While it's true that hotels pay more, we don't own/manage multiple properties.

The house is easily worth $305,000 and rents would be about $2,200 so at $220,000 it would be a great rental to add to our portfolio BUT, the contract says the buyer has to lease back to the original owner for 30 days and it will be sold sight unseen.

Am I just looking at the wrong property managers? 

Are you trying to create some type of cash flow from the portfolio to be able to leave your job, or build equity and appreciation to be able to extract and move into the next deal?