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 It seems like a lot of double handling of the money and going through exchanges you might be hit with KYC.  If you could buy a prepaid debit card in bitcoin, or have a credit card that accepts bitcoin, this would work much smoother. 
 It is a lot of double handling but I find it worth to live on a bitcoin standard. My exchange where I do most of this will be issuing a credit card soon that will pay off with bitcoin automatically. In the meantime, I do the extra work based on first principles. 

Personally I’m leveraging my software development team to build more tools that will support bitcoin as a unit of account that will work with the financial solutions that will be forthcoming 
 My problem here in Japan is the KYC on the exchanges.  I bought the majority of my bitcoin before these policies were implemented and i don't want to dox myself.

What is the name of your exchange and do they have KYC policies?  I would love to get a bitcoin credit card. 
 It is https://www.getbold.io// but I think  it is only available for US residents and do require KYC. Sorry.