I have not had him insure any rental properties yet but he was recommended to me by a fellow seasoned REALTOR® and investor and has been fantastic so far. 

I was fined for over $400 for using garage as storage.

I’m a seasoned remodeler, licensed HVAC, business owner, and a LEO.

@Brian GerlachHow do you do businesswise with the slow season of the fall and winter months or have they been slow seasons for you in your experience in short term rental arbitrage?

Once we get to a certain point (not sure what this point is yet), we will switch over to growing the portfolio through acquiring small to medium sized multi-family housing, storage units and mobile home parks.

Assuming it needs work and wouldn't qualify for conventional financing a hard money lender is probably your best option then refinance once you pass the seasoning period.

But we're looking at building up a solid rental and hopefully self storage portfolio so we have a solid base in case vacation rentals aren't as profitable as we hope.

You want to see something that has low or no seasoning for a cash out refi or that may require low amount of documents.What is your draw fee & benchmarks for the repairs portion of the borrowed money?

That’s the issue as the island is seasonal.

That way I could easily see profits per unit and admin expenses/total business health all in one place while still keeping all of my documents, tenant leasing and contact history, etc. right now I am just too spread out using Quicken, Tellus, Evernote for document storage (receipts, bills, quotes, etc), and OneNote for process/procedure documentation (my eMyth planning In Progress).