Some ideas and questions I have around best approach:Do we continue to put our own money into these repairs to see through the work on the home or is there a loan or HELOC that should be considered instead?

We send our clients  a comprehensive list of what we see COULD be fixed, as we have no idea how each owner will want to maintain their property(s). 

Do you have an idea of how much you'd rent out your current home for to a tenant (and what the resulting profit would be)?

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

I'm going to turn your idea into swiss cheese here, so don't get offended - maybe it will let you consider other angles here.1.

But of course the gurus will still take your money and not give you any idea that what they are teachingis legal or not..

Any idea about this?

However, since you already own a duplex and SF one idea is to invest in what you already own.

A thermal camera inspection would give better idea if its because of cold air getting in or the room does not have enough hvac / heat source

You want a hustler, not a top performer, if you want check-ins.I appreciate the candor and would definitely agree that my framework is all in theory until I can get a proof of concept for these out of state deals.I like your idea of pushing my boundaries in CA.