If you have enough folks coming through, it could generate more cash flow as a short term unit than a long term unit.We just added a guest house/efficiency style two story apartment in the garage building we have.

My question is after I scale up and make enough cash flow to sustain my life style I’d like to quit this job.

Anyway, what you've described is certainly achievable.

Maybe get a consult from an interior designer, you can find them online and often listed by the style they specialize in, etc.

You would need a 4-plex to achieve that goal.

It is definitely one that requires problems solving skills in order to achieve the greatest results.It sounds like you’re fairly open to trying anything that might work.

I have read many articles, watched videos, podcasts, etc and without over the shoulder style help and mentorship - I am unsure how to move ahead. 

Google what the exact benchmarks are for achievement and keep doing those.

Cash flow is achievable in the city just be careful of not falling into the trap of a C/D location that has great cashflow.

Now, ever since we shed our retail management division, the boutique TK experience is something that is repeatable, owners and tenants alike that we serve are able to receive not only our undivided attention but actual measurable and consistent results - that's what counts - you have to have a process, you have to have a STANDARD and you must be disciplined to achieve maximum results, everytime!