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and only after you covered properly the "other" aspects of risk management (insurance, umbrella insurance, proper property management, etc.).Here are some visual diagrams to help you in your quest:Asset Protection Decision Diagram - to help assess the need for asset protection, and what to implement : https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-decision-diagramAsset Protection Onion Diagram - what, when and at what cost one should implement in terms of asset protection - https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-onion-diagram-v2What is needed for a complete asset protection OR the domains that need to be intersected to find asset protection

But something to definitely considerBut the purpose of the post is for actual user feedback of institutions others are using that they recommend.   

He also told me that he spent the last 10-15 years off and on homeless and was a drug user who's been clean for the past 4 years. 

Use real estimates, but also factor in rent increases over the years and what condo/HOA fees are likely to do as well as major repairs. 

If no one wanted to live in coastal California the real estate there wouldn't command the price point that it currently does, Im just speaking fundamentally of course. 

If you have a $6000 per month interest only payment and the best case scenario is renting both units for $5000 per month (you only mention renting one unit for $2500, perhaps the other "owner" unit is far nicer and commands more rent?)

If this property has big defects you should command a discounted price.

Not user friendly.

It has a lot of users still.