This will consume multiple years of cash flow to recover the initial negative position.As you indicated, the issue is not only that the initial negative position consumes years of cash flow, but it also implies the ADU investment cannot be extracted until appreciation has been high enough to make it possible (this could also take years).My initial protege had a 1 BR garage conversion ADU that hands off would have been ~$100K (value just before COVID, it would cost more to build today). 

I may extract equity later through sale or refi. 3: Hopefully property will increase in value but I didn’t model it in since past returns don’t indicate future.

The question here is how should I leverage the equity I have built here - I could sell (also due to question #1) and reinvest the money else where OR extract equity out of this (HELOC or refi) and invest elsewhereI'm happy to clarify to help me get better answers.

So the pattern is to keep the provisions for this type of property ownership on a short leash because of all the bad experiences residents have had with the slum next door.Therefore it is incumbent on us to establish a different narrative that shows how investors "invest" in communities rather than "extract" from them. 

However if I do a BRRRR I can achieve infinite return by extracting all of my investment.

Mom and pop extract the increase every year.

Couldn't agree more about extracting yourself from the rehab as much as possible, especially the physical labor part.

(That said, it's a bit annoying when both have the same 5% category a given quarter.)CFF and your CFU also work really well together if you get a Sapphire Preferred (or Reserve) card in the future (aka The Chase Trifecta) as you can extract even greater value from the points if used for travel.

Solar would increases the value from an appraisal stand point but the market extraction for the cost incurred would not make sense. 

You're still choosing to pay or your own money when you transfer it from your bank (free) to the equity (cost to extract).How/when are you getting an extra 150 in "hypothetical" cash flow?