If they try to pay their labor as 1099 they run at great risk of violating a host of draconian labor laws such as AB5, the borello law and a litany of "misclassification" laws.There are substantial differences in how "right to work" statstate as operate as opposed to "non right to work" states.SBA defines a small business based on employees and revenue size.

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.

I can buy a 2-4 unit with 20% down vs conventional can only buy a 2-4 INVESTMENT property with 25% down 4. there are options where DSCR loans dont repot to personal credit, helps in not having to show a bunch of paperwork or not one person in a partnership has to carry the debt5. way less paperwork to close on this loan type vs a conventional loan. we care about the income of the property you're buying and it's ability to service the debt of the property whether we use long term rents income, lease income, or air dna/bnb income.6. easily buy in partnerships, add people to your operating agreement, its as easy as that so bring partners into a deal. helps with scaling and raising capital or getting partners involved7. gift funds allowed to close on these as well, and like I said earlier, there's only a 10day seasoning period of funds with some lenders so that means you can literally have a private money lender deposit money into your account 11 days before closing, and you can use those funds to close!

Cash-flow is for "keeping the lights on" as in covering operational expenses to defend against any need for additional capital investment. 

Living in a great travel destination like Sonoma you should consider a duplex or triplex and operate the other unit(s) on AirBNB, VRBO, etc.

They don't buy it and operate it.

There are a ton of tools and resources that not a lot of people know so doing some YT watching and their training helps immensely. also, happy to answer any questions you might have on set up / operations.

On a commercial asset the value is directly based on the NOI (net operating income).

Buying fent from a stranger is a safer bet. 

Any pros/cons on either or any other operator suggestions would be greatly appreciated.