I suggest connecting with someone that can sit down with you and run each of these scenarios with estimated numbers to get a better idea of what is realistic and what isn't.

Run the numbers you may do better long term or renting as a whole unit.

In my view, regular home insurance is really no different, and adding the Aircover makes it better than any insurance I have seen.I see that STR insurance can benefit people who can’t utilize Aircover though.

You clearly misread the market here and could have done a lot better IMO.

I've learned a lot over my time investing in small towns and have found some great opportunities but just like any other niche market you better learn what you're dealing with or you'll get burnt.

I would love a calculator that could help me make better decisions but not sure that exists.

They will be able to guide you through setting up financing, creating an investment plan, getting subs set up, and creating an execution plan.A good investor focused Realtor should be able to guide you on what markets you can afford, help you focus on your personal risk tolerance, and find a property that fits your skill set and financial goals.The more educated you are as an investor the better, but the right Realtor is going to unlock a wealth of information that is going to super charge your knowledge of investing, and help expediate your plan. 

I agree with the other contributor that it’s better to own a $1M asset that appreciates 3% per year that pays no cash flow (over the long term) rather than a $100k asset that appreciates 3% and pays $300 a month in cash flow.

I do recommend creating (and keeping updated) written policies for all of your leasing and screening process, and making them available to folks during the application and screening process (talking about, sending links to, emailing, & reminding, the more times they see it the better even though they likely won't read it).

At that point, it's worth researching and finding a solution that better meets your needs.