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slowly start onboarding merchants around you, once you are comfortable with teaching others, small steps and climb the slowly the ladder on more complicated solutions
This is nearly impossible to do an a large metropolitan American city
But everything else on your list I pretty much do!
In the beginning you do not need all the merchants onboarded. Is enough a single one (the smart one) that is willing to offer you anything you need for your sats. The small "mom&pop" shops are perfect for this. Will be like your "personal amazon shop".
I have a shop owner doing that for me for years now... he even offered to pay all my fiat bills in my name. Anything I want I order through his shop (is a small grocery store).
But the important part is not how to spend, nowadays we have so many places where to spend easily. The important part is to have a constant flow of sats into your wallets and do not depend anymore of fiat banks.
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