I should be able to mitigate this myself by doing diligence on the property before investing, and assumedly, so would he.

but you earn a lot but there are ways to mitigate your tax burden.. ( airplanes  Bulldozer etc)I get the buy and hold but that for most investors is a slow build up.. in the flip game you can make realistically 100 to 200k in a year ( taxable of course) with the same capital in buy and hold that might make you 20 to 30k in cash flow.. its all about how much time you have and how you want to finance all of those rentals ..

I always structure my client's portfolios so that they are holding each property in a different LLC in order to mitigate the risk of damages from one property affecting another.

I would cya and have documentation, like receipts for all the mitigation you do, to show you are putting in a good effort.

Consider taking on a low risk property to mitigate? 

 I had some financial difficulties in 2019 and defaulted on 3 payments.  I was offered forbearance for 6 months in 2020. My financial situation improved in 2020 and have been making regular payments since 10/20. A few...

Perhaps I've just been lucky, but in my experience if structured correctly there's minimal risk with a subject-to transaction to the buyer (and each of the items you point out can be mitigated with the proper documentation and title insurance).The key to staying out of trouble is fairly simple with a subject-to...keep making the monthly payment.

But rarely is there specific advice on how to best mitigate these risks. 

I haven't been able to find any definitive info on this.On items 8) and 9) can't this be mitigated with proper disclosures and release of liability agreements?

Insights into prudent investment practices, risk mitigation, and strategic decision-making would be invaluable to me.📚 Continuous Learning:As a first-time investor, I am committed to continuous learning.