Honestly, you'll struggle to find too many good books or articles about deal making since it's not really that complex of an issue.

The higher you feel the level of variance is going to be at the final table (i.e. if stacks are short, the structure is fast, or if all the players are of relatively equal skill level), the more inclined you should be to chop. The shorter your stack in comparison to the field, the more you should be inclined toward taking an ICM chop, and if you're a bigger stack a chip chop is going to favour you.

If you feel you have a significant edge at the table, you should be less inclined to chop. If you feel you're outmatched, you should be more inclined, but bear in mind that better players will most likely know they're better than you and turn down your request to chop.

Never be the first person at the final table to request a chop if you can help it, at least not until you get 4-handed or further. This is a little bit of a signal to any stronger players left in the tournament that you're likely to be scared money or playing more passively/tighter. The guy who requests a deal as soon as the final table begins is always the guy who plays like a huge nit the whole time.

I tend not to chop very often, but I'll do it sometimes if it's a particularly big final table or I don't want to have to spend 3 hours playing 120bb deep HU in a $11 freezeout. In general, you're probably not going too far wrong if you only consider chopping when the money at stake is very significant to you. In those cases, if you want a decent deal, you're going to have to be prepared not to get one – if you're the guy begging for a deal the whole time, the chip leader is just going to pound you into the ground.