It's so natural to be skeptical and so easy to stay safe and maintain the status quo.

It is free to use for hosts and guests.

You should check out the Straight Up Chicago Investor's Podcast for a lot of local market knowledge that the guests have shared.

In my market, I've seen the aftermath of an investor getting caught running an illegal (by zoning) vacation rental...it was all over the papers and local news - and the worst part was that the guests were kicked out by the municipality immediately upon discovery...and that's not great for reviews or continuing as a host with any site.

I refer these guests to Airbnb support to request consideration under their policy.What say you?

PLUS we have photos of the unit exactly as it was when the guest arrived (which comes in handy much more frequently than you'd expect (being able to send a photo to the guest with an arrow pointing to the extra toilet paper is next to godliness))

This seems excessive for a 1 month stay but if they turn into nightmare guests it might be needed.

i called my grandparents as they have a unit there and was just inquiring on the status and costs of the area. 

Given you already have started to build out a portfolio, you should also talk to your accountant about qualifying for real estate professional status to write off losses against ordinary income - https://financialresidency.com/real-estate-professional-irs/.

If you would prefer to coordinate the work through a contractor yourself, try to confirm that they do quality work and communicate well so that you are aware of the status since you are not local.