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

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.

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.