Also, the roof is a barn-style roof, so it starts to slope at about 4ft high.Is there anything I should add or change to suit MTR (and STR in the gaps of no MTR guests)?

I also plan on moving the master bedroom (currently upstairs) to the other ground floor bedroom, and making the upstairs bedroom a "guest room."

With a large group of say 16+ guests a $2000 or $5000 weekend is much less expensive when multiple parties are paying.   

I would be mad.Just get a charcoal grill and let the guests supply their own charcoal.

If you rent the condo out to others it would be the same thing -- you would need a policy that only covers the interior walls -- it would be an HO6 tenant occupied and depending on the carrier you currently have you would either change the occupancy status or you would need a different policy-- in my experience 9/10 times they require a different policy. 2.State farm does not really ask a lot of questions -- their quoting process is not as in depth as it should be.

If you achieve Real Estate Professional status, you could potentially drive your income down to zero, minimizing your taxes.

Cleaning fees are a pass through from the guest, so you would be receiving the payment from the guest within a short time after check-in and then you can directly pay the cleaner with the cleaning fee you received.

Sounds like your target market (or guest avatar) is fisherman/outdoorsy vacationers.

Unlike Airbnb, no one can cancel their trip midstay without my ok and there's no one issuing refunds to unreasonable guests without even consulting me.

It's possible to anticipate paying between $1,500 and $3,000 annually for each unit, but to fully grasp the range of expenses, it's critical to obtain estimates from several insurance providers.If you intend to keep one unit unoccupied for guests, a triplex could be a more practical and affordable choice.