First my complements on your tackling a cocktail pin. These are a sorely neglected branch of the pinball tree. I'm excited to see this project as I'm beginning work on one myself. I'll be following your build closely for ideas and identifying pitfalls.
Putting yours up on legs answers one of my criticism of the form which is they don't normally nudge. Since I need to keep mine low I'm struggling to think of some way to float it on a suspension.
Thank you for pointing out the limitation of cabinet depth. I'll have to keep that in mind.
Regarding cutting your playfield. If you have not already figured out these tips, I have a couple. One way to work around losing steps causing inaccurate x and y, is by cutting the playfield incrementally (sling shot holes, pop bumper holes, roll over slots, outside edge, etc). Having your workflow incorporate a homing step (reestablish 0,0) at that start of each category will keep the errors from accumulating. That way if the machine loses a few steps, the errors do not add up with each cut. As I think you identified, shallow cuts improve accuracy. I never cut more than 2.5mm myself.
On the metal bending, your ball guides look great. I had a lot of trouble getting my mounting tabs to bend exactly where I wanted them. My work around was to weaken the metal where I want the bend to land. I did this by drafting a tiny notch at the "ankle" of the foot. I use a 1mm radius half circle on either side of the bend point. Then, when I go to bend the metal, it naturally wants to fold there. This allows me to get a 90 degree bend using merely a vice on the ball guide and a few taps with a small hammer on the foot.
Thanks again for taking the time to post your development.