He's a pretty smart guy, and if I can point him in the right direction, I know we'll have another convert (lol).I live in Washington DC, so I know the market is dramatically different, and I'd like to give him local advice. 

Don't think I'm being over dramatic.

Although my counter argument would be is the risk of a black swan event to the S&P 500 is dramatically lower than that of a black swan event to any single property. 3) Agree.

I recommend you print, study, highlight, and learn this because the use of ESA exceptions is increasing dramatically as more renters learn how easy it is to cheat: https://www.hud.gov/sites/dfil... 

Rates have had a pretty dramatic improvement since yesterday’s fed announcement. 

That cost will vary dramatically bases on who you use and what is your relationship with them.

It will dramatically increase the number of new homes available in California.Status as of 9/16/19: AB 68 has passed and is headed to the governor’s desk.Learn more about AB 68.......(2)https://www.hausable.com/adu-guides/california-takes-another-big-step-to-promote-adus-statewideAB68 & AB881 (Overlapping bills)Removes minimum lot size requirements for ADUsReduce maximum setbacks applicable to an ADU to 4 feetIncreases the size limit of an ADU substantiallyVoids FAR, lot coverage and other standard's applicability to ADUsReduces the max approval time for an ADU to 60 daysExempts garage conversion ADUs from replacement parkingAllows for up to 2 ADUs on multi-family propertiesAllows a single family property a conversion ADU and a JADU per propertyQuestions:- what is the right interpretation of having two ADU/JADU per property ??

It really depends on what area you settle on as what's allowed varies dramatically.

When you don't want roommates, your options dramatically decrease. 

I hope your county has an in person auction my local area has going online and that has dramatically changed the landscape.