I use a small percentage of my Pro token quota to find better deals on hotels, rental cars, discount codes for large purchases, etc. Have it automatically scanning credit card points promos and flight deals via various APIs too. Easily pays for itself in that regard. Over $1k, I'm not sure it would break even anymore.

Does ChatGPT have the same large enterprise restrictions as Claude, where teams above a certain size are required to use API billing?

That would limit the $500 plan to smaller businesses.