Below, i provided a few questions. 

I'm confused, can anyone provide some insight?

Do not provide substantial services 3. average stays of 7 days or less4. materially participate Primary Residence route:I presume that doing this route will:1) portray yourself less risky from a lender's perspective2) Less downpayment requirements.

A 1031 exchange would likely only cost you a fee, plus impose rules on how to use your sale proceeds and when, without providing a tax benefit. 

You really need a team that provides rentals, All the best 

I have a wealth of knowledge I can share with you and provide you with some good insights into markets to avoid and those to pursue. 

Also, what exactly was the quote provided by the contractor?

Any guidance provided would be greatly valued.Having said all this, we aim to do more than just scrape by month to month for the next year or two.

And I also realized that I wouldn't make a claim unless I had a major loss anyways, as it'd likely make my premium skyrocket (and would perhaps make the provider not want to renew at the end of the year).

. - Contractors- Capital providers: JV partners, private money lenders (PMLs), hard money lenders (HMLs)sFor additional context, are you going to be flipping and actually selling or are you going to be fixing and holding for rental income?