I have noticed that his capacity and bandwidth has been reduced as he scales into commercial and other aspects of his business.Has anyone successfully tranistioned from a strong mentor to independent investor?

Tenant A brings familiarity and a solid track record, which definitely reduces some risk.

House hacking builds equity and can reduce your house expense. 

The property is held in his corp, but I’ll get a personal guarantee, and if appraisal value is lower than expected , I’ll ask for cross-collateral or reduce amount loaned out.

Adding a water leak sensor or protective measures to prevent damage might mitigate the risk.

Please see this website:Lead Prevention | Toledo Lucas County Health DepartmentExpand the portion that says "Before Purchasing or Selling a Home.""

Prioritize Preventative Maintenance: Regularly inspect properties and handle issues early.

Your biggest focus in investing is to first ask how can this go wrong, and how can I prevent or mitigage.Murphy's law paraphrased.. if you dont prevent it, you are asking for it. 

With personal debt at all time highs, people's ability to repay, prevents loans for housing going beyond the current level.

I either drop it, pay the exorbitant premiums, or reduce it somehow and only have liability, if I can.