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? 

And while you may not be a titled owner, as a relative you'll likely be considered as such if you end up in court since its obvious you're not in the business of PM.

Do not kid yourself as when you sign with a management company you sign a business partnership.Eventually I do not want to manage my properties and I will look for a manager who can get better returns than me, maintains properties and has fair terms on the partnership (charge a fee share the fee except logical fees like cleaning fees).

What is your actual business plan?