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.

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.

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/

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 thought of LVP but I'm not sure if it's a good idea in the bathroom.

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

If you end up in Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods to give yourself an in depth idea of the market.

Still open to market ideas (so if you have any ideas, please share!)

I definitely like your ideas of focusing on location and trying to get my downpayment closer to 10% rather than 3.5%. 

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