How about a scenario where an individual is buying art / crafts produced by Thais in Thailand to ship and sell abroad? Surely this is completely beneficial to local Thais. What would be the legal status of an individual doing this?

If the indivdual buying arts and crafts in lives Thailand, in essence you have an export business going on, therefore would require a WP.

I'm thinking of a situation of being in Thailand on a tourist visa for a few months per year, on a buying trip so to speak. Somehow this seems like what any tourist does, buying souvenirs to take back home, but then the intent to resell items abroad or the volume of purchases shipped out may change the status in the eyes of the law I guess.

Normally that should not be a problem, but might also depend on who takes care of the export to your country. In general a non-B visa will be enough if you just have business meetings. In case you take care of the export yourself, it might be streching the rules and considered working.

The same grey area applies to photography, where any tourist taking pictures is technically "working" according to the all encompassing definition from the ministry of labour. I guess they reserve the right to penalize anyone at any time at their discretion if it suits the particular official involved at the time. A real lousy situation.

It seems the condition of being "freelance / self employed" is pretty much akin to being "Stateless" according to immigration (not only in Thailand). Hopefully the freelance visa that's been announced will adress this somewhat.

Ah yes but what if he sells his art / photographs online and someone from thailand buys it over the internet?????

How about this case: An artist (painter/photographer) or an author, who likes to spend time in Thailand, is content with a 30 day stamp in his/her passport on arrival, and tourist visa from neighbouring countries, ... sits in his private space to draw, paint or write, .. has no interest in having clients in Thailand, never shows his work in Thailand, because all the income is generated from business outside Thailand, > publisher in the UK > galleries in Europe etc Stays out of everyone's way, ships his work out via courier, in his luggage or in the case of digital files, via the WWW .. does not take a single Baht from anyone in Thailand, nor competes with any local "wanna be" artists, so jealousy is nothing to contend with ....

If that were you, would you even worry about a permit?

If it is delivered from the USA then it's not a problem. If it's delivered from Thailand then it could be a problem.