It's often because people don't want to do the research or work necessary to get prepared to invest so they do things like talk about LLCs, scaling, and look online at hundreds of properties before ever seeing one in real life.The antidote is to go to real estate investing meetups, as many as you can, and never miss.

If you are able to sell it as the listing agent and keep some of the realtor's fees, might be a bit different. 

I'm talking (2) $60K duplexes, and one $125K fourplex all above 2.2% rent to price in fair/good condition. 

Because later, you can easily use it as your mailing list!

I really wanted to use a PM, but at this point I'm seriously contemplating just letting my RE agent list it, screen the tenants & get a good handyman, plumber, electrician etc. to handle whatever issues come up. 

Real estate is a long game unless you are talking about getting a real estate job, which then requires skill and experience.

Can you talk to other Berkeley landlords doing ADUs to get their feedback? 

What is everyone's protocol if I get a lot under contract for say $20,000 and then go list it on the MLS as assignment for $28,000.... then the owner sees it listed (through Zillow or another avenue)?

Talk to a local realtor who works with investors to see if $2600 is realistic for rent and who you'd be marketing to-likely a smaller tenant pool.Most people who rent fall into different categories-those who are just starting out and saving to buy their own home, those who move around and buying doesn't make sense and those who will never buy a home (either can't save the down payment, can't get approved for a mortgage or plain and simple don't want the responsibility of owning a home). 

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.