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I've been on both sides of that (or all three sides if you count the vendor, too).

Boss: use it to leverage either a better deal, or extra support hours, or make them package it. (Unless it is Oracle. Then you just bend over).

Tech: Tell the boss exactly how much it sucks, and how you wonder if this vendor actually knows what "operate at scale" means. Take the extra support hours and get them to write an installation package.

Vendor: Oh, shit. Another thing to add to my list of 1000 things to do. Is this or feature X more likely to be useful? Damn, let's just offer extra support hours.

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