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States want their share. So many convenient ways to purchase used to fall under the radar - no longer. In RI I have to report all personal sales each quarter of my book and pay the sales tax. I might sell a half dozen personal sales per year - maybe $100 - still have to pay 7 % on each sale. Also have to declare it as income on my annual return.
I run an AIRBNB and my guests are charged 13 % for state and local sales taxes. I'm sure Uber adds sales tax.
Years ago there was a reason BM plugs were all sold to retailers without receipts and invoices - but you're taking a chance in today's environment with all the tracking technology.
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