Considering your existing business experience.

Hudson is a pretty "touristy" town, so BnB's became a big thing and the local gov't was concerned about the amount of long term housing available.

Hi Daniel, Columbus GA has properties much lower in price than the metro Atlanta area, you should do fine to learn your local market.

The risk of "piercing the veil" applies more to LLCs when personal and business finances are not properly separated, not necessarily to individual landlords renting a portion of their home.A more practical approach is ensuring you have a solid lease agreement, sufficient liability insurance (including an umbrella policy), and properly reporting rental income and deductions on your tax return (Schedule E).

Anything you do remote will come at a cost of operational inefficiencies and a higher cost of doing business.

And, Turbo tax Business software is $163.

I don't need to worry about anything with Umbrella, but for LLC, I need to follow the operation agreement and keep in mind not mixing personal and business bank account.I'd like to know what are your thoughts, and how do you make decision in this case?

Also if there are any local mentors in my area who would be willing and interested in helping me out I also am connected to Michigan as well! 

If you’re comfortable with the process and local regulations, new construction might yield higher equity, but for simplicity, an existing duplex is safer.

If you are considering looking in that location, I HIGHLY suggest you connect with a local expert like @Josh Green