The fact that they have received so much insight by being able to watch and observe you will open up a whole lot of opportunities for them if they so choose. 

I know several investors who choose to represent themselves, but they often end up netting less than they would if they had an agent.

Take short-term rentals - they do provide several tax benefits, but they are hard to run and very hard to succeed at so people make the mistake of choosing the tax vehicle, get the benefit, and then lose money on the investment and hate it.

That's why we started offering BRRR Turnkeys, where we help investor source a property (or they can find on their own), we rehab it, supplying rehab videos so they can see what was actually done.

I am an out of state investor and in the past I have purchased my properties based on video walkthrough that my (trusted) realtor does.

I have made 30 videos on how to do things and put them on a YouTube page for our tenants, sent it out on an announcement, etc.   

Does anyone have a similar experience of living in the heart of a city but choosing to mostly invest in the urban sprawl outside?

Meaning the at the end of the lease, the tenant has the option to buy (but not the obligation) whereas the seller has the obligation to sell if the the buyer chooses to buy (works just like selling stock options!)

I'm assuming you haven't achieved mastery in all 3 categories, but realistically you can choose from 2 of the 3 categories.

If you choose to sell, consider post-retirement timing, installment sales, or a 1031 exchange to mitigate taxes.