I think you'd be better served to turn the STR unit into a long term rental.

I have about 5 years experience with short term rentals as a host/co-host.

Together, we negotiated favorable terms with the seller, ensuring a beneficial deal.

I grew up in the suburbs of Chicago and would ideally like to invest in IL since my family is still there and can serve as a home base for whenever I need to be in the area, but with IL property taxes being as high as they are I'm also scoping other markets in nearby states.Does anyone have any general advice for buying / investing long distance?

Purchase price: $234,900 Cash invested: $7,000 I house hack 2 bedrooms in a 4-bedroom home as Mid-Term Rentals.

I am currently reading "Long Distance Real Estate Investing", by David Green (published by Bigger Pockets) and decided to apply some of the analysis to a currently listed deal on NORADA. 

Refinancing doesn't make sense as I'd effectively double the current interest rate and have additional closing costs surpassing the PMI. 

It's smart to have more than a few conversations because not everyone offers the same products, leverage or terms.

I currently own my primary residence and recently decided to buy a piece of raw land where my father’s construction company is, and with his help,  build a single family home on it which will become a long term rental when completed. 

If you're not planning to live in the property long-term, I'd suggest prioritizing the property's standalone investment potential during evaluation, regardless of its role in a house-hack scenario.