If the tenants are great then it might be worth trying to keep.

One thing I have found over the years is that trying to find the cheapest prices on every item often costs more in terms of time wasted that it is worth. 

The owners still owe about ~58k and I think the house would be worth around $110k-$125k once renovated.

Maybe it's worth paying for a Facebook ad campaign.  

Would it be worth it to convert a multi-family from window units to HVAC?

Would it still be worth it if I'm still having to pay around $1,500 a month to live there?

But I'm making it work, the trouble is worth it in NELA, but probably not in some locations.

Well worth the time and membership fee!  

It's important to remember that short-term rentals are subject to fluctuations in demand, so it's essential to have a solid understanding of the local market conditions and the property's performance history.Google awning airbnb estimator and take a look at the seasonality and performance of nearby Airbnb's to really get an understanding of how it might do

I understand you're looking for a good area with good growth at a good price in the Tri-State Area but if the numbers aren't making sense, it could be worth check out the market in the Midwest specifically in Ohio.