So when you build your pocket neighborhood, which is an interesting concept, what's to stop an undesirable person from moving in.

My 2 cents would be that since it is your personal property that your CPA is right but im far from a tax professional!

For my own personal goal reasons, I am going to still with searching for a lender who will be open to it.

I started investing about 8 years ago personally, then decided to become a professional a few years ago. 

Happy to connect and chat further!

Determining whether the venture falls under a service or rental business hinges on the provision of substantial services; for instance, if a bed and breakfast service is offered, it must be reported on Schedule C, triggering a 15.3% self-employment tax.Moreover, personal use plays a crucial role in the classification of the property.

Hi @Danny Krish happy to chat with you about real estate in this area!

I personally like to manage the risk and take it slow and true. 

Sometimes people who are comfortable managing the details of a job will hire a less skilled person to do it knowing they can get a MUCH better price and a "decent" job IF they themselves stay on top of how the work is being done.

Either A) you need to want a ski Airbnb/VRBO for the personal use of it but not the investment aspect of it or B) you need to be okay with some of the areas within 45 minutes of the ski areas that are totally open to short-term rentals and where the numbers are better.