I've also devoted a substantial yearly budget to continue education, including strategic, legal/title, transactional and very advanced sales and marketing.Lastly, a chunk gets returned by way of charitable activity and contributions.  

I'm not afraid to raise rents, and I don't think any Santa Barbara area renters think that SB landlords are particularly charitable : ) The big obstacle to bringing the unit up to market was money.

I am looking at creating a single member LLC Trust, for our multi family units, not totally because of lawsuit protection, but because they are highly leveraged and our SFRS have a ton of equity, and I am setting them up for future charitable gifting. 

I dont sense much charitable notion on the board.As for your desire to retire with passive income from RE, Doesnt just about everyone hope to retire at some point?  

Or if he's not trying to be charitable, have him refi and pull his money back out while cash flowing and do this all over again in a few months!

Take advantage of all available tax deductions.There are many great tax credits such as charitable contribution credits, green tax credits, real estate tax and employment tax credits.

The charitable giving will keep his NI down for years along with depreciation and interest expense.  

The overall impression I got from others was that it would be better to either establish a non-profit or to go the traditional route and pair it with charitable donations on the side.  

In October, he quietly merged his charitable arm (Musk Foundation), founded in 2001 in California, with a newly created entity in Austin.Dec 15, 2020from observer.com

I find this post on BP to be confusing as this is not a website for sharing ideas on how to be charitable to others, which sounds like your biggest motivation based on your post.All that being said, the details you have provided appear to me that you would be taking on potentially significant risk.