@Adam Bartomeo runs a professional property management business in the area and is also a long-time member of BiggerPockets.

Once you experience and understand the business better you can always flip down the road.

If I was to somehow turn my rental into a business, would I start qualifing for business loans etc. through the Sole Proprietorship or LLC?

You need to build up your network as this business is all about relationships. 

We are considering purchasing an income making property and business combined, 10 acres 3300 sq ft home and barn.

The way I see finding members for your team, whether it be your tax professional, legal, PM, and so on, is simply understanding things at enough of a level where you know when interviewing them if they understand your business.

My primary residence is owned in a family business LLC.

New investors often want to know how to get started as it pertains to Hawaii specifically, but I tell them the business is the business.

Has anyone started utilized AI & ChatGPT into their business? 

What is your actual business plan?