Selling to an investor basically mitigates questions 3-7. 

(Before inspections were done from the BHFDP now the new person is a local well known building inspector with years of experience and owner of his own building inspection company, he will find something if it is wrong or right and he will point you at the right direction how to fix it.)Last 10 years the rental market including hotels has only increased, we are likely to see some drop but not a full stop.Majority of tourists are coming to town within driving distance, that includes, NH, CT, MA, NJ, NYBar Harbor will have its struggles I am sure, your neighbor might hate you for having STR but with the right management you can accomplish a lot and mitigate risks.Anyhow, there are some valuable advices above and I would suggest making peace with yourself, that good management company will cost part of your income, but you may not even have to lift a finger.There is a lot to learn, but been busy making great income on your w2 is it really worth "learning another trade".So much to learn especially with the clientele we get.Building reviews the first season is very important, having a co host someone with reviews and local experience can be more valuable than any other "online non personalized service"Anybody that just red my novel, thank you!

I'm sure there are good ways to mitigate all of these but this is just my 2c.

@Nick Gee, Your entity structure is more about liability mitigation and operational tax efficiency. 

We mitigated with strong covenants and building requirements with a design approval requirement. 

I want to bring a partner in to mitigate risk and also cut down on the amount of capital needed to fund the deal, since most of these homes are in the 650-750 range.Is the logic sound here or am I missing something on how this loan could work?

The inspection companies I've contacted offer a pre-purchase inspection that's very thorough, but my realtor is telling me that I need a 5-point inspection and wind mitigation for insurance purposes, and a termite inspection.

Don't get caught up on buying a homerun with your first purchase, get into something, know the numbers, mitigate risk (great locations), and then scale from there.Good luck. 

Mitigating those typically comes with experience.I have investors invest with me passively as a syndicate but these are dark buildings already existing and easier to turn around than ground up developments.Right now it's hard to build one off spec projects.

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