He told me he contacted them to see if they could promote the project.

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.

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

.- 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?

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. 

We want to be able to create an estimate for a project and then track everything back against that estimate (Labor and Materials) to see how we are performing on each project.

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.  

Lol :-)For some reason "Subject To" elicits responses like a steak to a Doberman pincher....So your saying this whole thing is just a Self-Promotion....