I'm also new to real estate investing and have experienced the same rollercoaster of emotions.

One workaround could be keeping a separate spreadsheet to track your adjusted tax basis accurately and only using Stessa for operational insights.You could also reach out to a cpa and see if they have a specific recommendation for software to use.  

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

Two separate property appraisers (at the direction of the lender) were sent out to appraise, and neither was willing to appraise it as a "residence", and thus financing fell through (conventional primary loan).

Once someone has paid, what to them is a good deal of money, and invested a good deal of time, and become emotionally involved with a particular mentor and his program, they’ll fight like hell to defend it.  

I like umbrella because there is no worry of being pierced for inadequate separation of finances, if sued you have a heavy weight in your corner who has all the consequences of a defeat, and because usually it is reasonably priced (mine today is not so reasonably priced but I believe it is mostly related to the risks of CA).I do understand that the probability of needing the umbrella policy is low.  

For most investors, to provide true separation would be cost prohibitive (between $10k-$15k). 

Open up another Optum HSA separate from my employers that allows me to link a Schwab HSBA, rollover funds from employer.3.

I have many questions about this topic - moving from self-managed to PM - I'll post something separately on this topic. 

This lets both parties separate rather than dragging out the relationship.