Purchase price: $375,000 Cash invested: $30,000 This was a 2 unit that I purchased in 2016 for $375K.

It is much more difficult to sell an entire portfolio that has become uninsurable (which would require a cash only sale) or that insurance rates are so high that no one wants to buy. 

However, you have to be extremely careful financing 100% of the transaction as you still need reserves, closing costs, etc. and make sure it cash flows.You didn't mention if this would be a rental or owner occupied. 

Yea the area doesn't look like it will appreciate much, I mainly look for cash flow.  

Purchase price: $940,000 Cash invested: $250,000 I purchased a Self-Storage Facility.

If the insurance isn't done properly, it's on the edge of impossible to cash the check because it's made out to the lender, my company, and the seller(s). 

Also, the whole point of hiring a PM is to handle tenant, maintenance, and rent collection, so if your partner isn’t actively managing but just supervising the PM, IMO not worth having a two people essentially looking over the same tasks.Contributing financially for one person and the other having no financial stake raises decision making questions, such as when to sell, how profits will be distributed, etc.

Is it worth investing in education or mentorships (WREIN is what I have been looking into but am skeptical).  

If you found this buyer I would say that its worth finding and then looking for the sellers but I believe that would take a lot more time than finding sellers and getting a bunch of buyers as opposed to just 1.

We've rented out some of our best investment properties (New Construction/Turnkey) to Sec 8 residents, and the rent guarantee always helps in achieving consistent cash flow each month.