Not realizing I was only getting a few hundred a month from it and from a cash-on-cash perspective I'd have been better off buying TBills with the click of a button instead of all the hard work, stress, time, and planning I put into it. 

As Sean above alluded to- never pay a seller for your future hard work, risk and stress. 

There's usually a good reason why the entry points are lower.

If they are legit and you don’t have any other offers then I’d have the conversation with them but I’d want a higher than normal down payment (ideally 50% or at least more than the normal 20%), a higher than normal interest rate (at least a point above the prevailing rate so like 9-10% right now, but you can structure it as interest-only payments so their monthly payment is still lower than conventional), amortized over 30 but with a balloon in 3-5 years, something like that.

I’ve been down that road of carrying a line of credit on a property before, and the stress can realy pile on when you’re staring at that monthly interest.

I’ve been working with several lenders for DSCR loans, but I’ve found that the fees are quite high, with minimal benefit in terms of lowering my current interest rate.

Are there any lenders who are lower than this, I've been brokering myself.

A professional property manager should handle the heavy lifting, ensuring your investment is protected and profitable without adding stress to your plate.

Top 3 reasons owners hire PMCs:1) No time to manage correctly2) No time to learn how to manage correcly: laws, documents, processes, etc.3) They're too nice and need someone to "save them from themselves"A good PMC can usually earn their fees by better managing the property/tenant than the owner, thereby:1) Increasing owners net profit2) Decreasing owner's time commitment, stress, headaches, etc.No matter what though, you should always plan to commit a couple of hours a month to manage your PMC.

If you are concerned it will be too hard to find a renter, lower the price and rent it for three months, then place a new tenant at the higher rate after winter.