The founder appears to have been involved in businesses outside of real estate: ‘My dream is a locally made grooming products business’ | People | nashvillepost.comSo it does not appear there is a lot of track record there, but those are questions I would ask.

As good as offsetting all his W-2 / Business income?

All contractors (no matter the trade) are businesses, and should be run as such.

When the whole covid shutdown occurred, I dropped out of college to help my father's service business maintaining and remodeling residential and commercial buildings.

But it is my opinion you should try Airbnb, VRBO, booking.com and FlipKey and give it a chance to see if it is adding business.

@Michael Quarles I can honestly say that I've never gotten any solid business from postcards.

Over the past 15+ years in this business, i have seen the good, the bad, and the ugly. 

This is a business.

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

The downside will have more to do with your business personality.