This has actually increased our bookings. 

Just make sure you are saving towards those slow months during the peak months, buy a deal at the right price (don't overpay just because its a turnkey STR or you think it will make more money than projected), and look into ways to increase bookings during those slow months with some marketing and operation tweaks. 

And over time, as those assets to make our product we sell had a fixed price, the dollar does not sit fixed, our cost of product increases meaning increased cash-flow.

Putting that amount into it will only increase the loss.

Rents have increased significantly but so have housing prices. 

That may increase your cost or limit the coverage you can get.The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policy.

I think it will increase down the road, but right now the town is a bit on the past.

I find it odd that this isn't a more standardized practice.

However, a full or partial gift means you inherit their $33K cost basis, potentially increasing your capital gains taxes when you sell in the future.

Largely, the appreciation in housing prices is coming from both new migrants and investors coming from the East (GTA) as well as international countries (predominately from the middle east).We are also seeing drastic increases in the rental rates which in turn are pushing investment property prices up as well.