I've correctly configured the JoinMarket Gui with Bitcoin Core. If I send coins through 3 or 4 depth levels, is this enough to "tumble" my coins for Circle.com? I don't want to lose my Circle account but I'm also lazy. Do I really have to use the tumbler script which means a crap ton of more setup? Thanks for your help.
The tumbler.py script doesn't require any additional setup afaik, however it does take ~10 hours on average to complete a run - and in my experience is prone to crashing.
sendpayment.py is definitely sufficient - you're sending first from Circle to your joinmarket wallet and then onwards. Nobody is going to bother tracking you unless you're a hotshot vendor.