Pat,
I just returned from making portrait deliveries out of state, so I'm in on this a bit late.
My accountant is quite clear about taxes:
If a painting already exists (say a landscape, still life or headstudy) and a collector buys it from your existing inventory, then you are supposed to charge sales tax... but if you are commissioned to paint for a client, you may be eligible to report your income as one who provides "contract services".
Artists that travel from state to state and even abroad for contracted work will find it very difficult indeed to keep up with all of the different sales taxes.
Setting up for contract services is more complicated and you will pay your estimated taxes quarterly, as a manufacturer.
You really should talk to a certified accountant, preferably one that has experience with contract laborers like finish carpenters, interior designers, architects and so on.
As to the subject of using the images of your clients....you simply must have their permission. Never use someone's image or name without permission and most certainly never ever publish images or names of minors without permission from a legal guardian.
I also let my clients know, that under no circumstances am I to be left alone with a minor...
a legal guardian must accompany us at all times.
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Joy Thomas
www.portraitartist.com/thomas
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