Now they are behind in electricity bills and I let it go since I took so long to fix the roof and feel bad about it.

You are going to loose out on a lot of income by doing this .If your cleaner cannot complete a same day turn - time for a new cleaner You would if you were running a 53 acre ranch in Texas with significant additional logistical requirements and maintenance needs (both expected and unexpected) beyond what an average short term rental requires.  

For those 2019 properties, even if they have fixed rate, long term loans, when the loan transitions from Interest Only to Amortizing, that can eat a lot of cash flow.  

I had analysis paralysis yes it’s a real thing, even if it’s just an umbrella term for a multitude of factors.

What is term of lease?  

Looking at a strategy to Brrrr or light rehab to rent out to long term tenants.

I'm  Bethany from New Jersey, just learning and breaking into real estate investing and hopeful to purchase my first short term rental property within the next 6 months.   

Are you looking to buy for your own account to hold and collect payments for the long term?

It sounds like you're saying to think longer term, to let things develop.

and are guests mostly short term or mid term?