The amount saved can dwarf $6k.  

I started talking to him about the minimum amount to invest, since I didn't know him or his company and he initially asked for $2,000 usd.

Just keep the amount within any local rules and give proper notice.

Hey Chris, a few thoughts here.Considering that office is not attached to the house, I wouldn’t add any footage to the total home square footage; however, you could advertise that office space and amount of footage and amenities in your remarks.If you’re a Realtor or are using one for the sale, your local MLS may have fields dedicated to additional footage for other buildings on the property, such as ADU’s.The other point is that typically, perhaps depending upon location, a space needs to have heating to count in the square footage, which this office doesn’t have if I understand correctly.Consider contacting an appraiser to inquire about how they would handle this space on an appraisal, or a Realtor.

How often is an individual successfully sued for an amount that exceeds their insurance coverage?

I figure if they don’t already have Netflix I’ll get questions on how to use it and my systems are all about the least amount of questions.

With 65 units under management it is a no brainer as the amount of time to price each unit daily would be a full time job. 

So let's assume you have significant enough equity in a property to pool together a reasonable amount of starting capital.  

.- Generally landlord-friendly state, no rent control- Secure government jobs/contracts make the real estate market much more resilient to recessions / major corrections- 15-minute drive to the Capitol of the United States- 4 Seasons- 15-minute drive to Arlington, Virginia (Amazon Headquarters 2 ((2017 announced, 2030 is bringing 25,000 new high-paying    jobs to the area)), Boeing Headquarters (2022), Microsoft Headquarters (2021), CoStar Headquarters (2024), Bloomberg    Headquarters (2017 expanded), Deloitte, and the list goes on)Thesis:Although more companies continue to go back to the office, there will be a shift toward a good amount of workers being able to be in hybrid roles.

There are definitely multiple options and some will allow for a set amount of personal transactions per year to waive commission splits.