Labor, materials, insurance, interest, local property taxes - yes.

I have another property that was an Airbnb for 7 years (now is a LTR) and for 2 out of the 7 years, it met all the criteria for the STR ‘loophole’ to apply and I was able to offset losses against W-2 income. 

Upon expiration of the 3-year period, you must provide a new Form W-8ECI.If you do not file a form W-8ECI with your property manager, your property manager is REQUIRED by law to withhold 30% of your income from the rental and forward the funds to the IRS.Legal Disclaimer: The material provided here is for informational purposes only and is not intended and should not be considered as legal advice for your particular matter.

This happened to me with a contractor who I paid a materials deposit to and he kept delaying so I told him to pay me the money back which he didn’t have.

.- I have the skill set to do majority of the work - the numbers appear do work well as a STR- the property has sat on the market for a long time (100+ days)- I am assuming material and substrates will cost significantly more then doing the same work in the lower 50 states.- the topics I search on BP appear to all be pre/mid covid, and have some recovery discussions post Irma.

I met the Material Participation requirements that year, and took our taxes to our preparer with the expectation of a refund. 

If I start running it as STR starting in June of this year, do I have sufficient time to meet material participation?

That is a very interesting statement, considering the material facts surrounding this transaction, and one could argue that it is disjointed. 

They (ins co's) wanted our industry (Roofing) to come up with better-longer lasting materials, like Class 4 shingles, so they wouldn't have to pay for replacing shingled roofs so often Fine, it happened. 

As @Jordan Moorhead said, make sure the renter checks out when requesting to book on the platform and use your specific screening materials or questions.