Teddy makes no sense

When you think of the character called 'Teddy', many things don't make sense.

First, when Lenny throws Teddy's car keys in the bushes, Teddy starts searching for them instead of finding out what Lenny plans to do. Would you? I mean, now you have this madman loose and you don't have a PLAN for him - WHAT plan do you think he's going to follow?

Isn't that quite darn important, and also, since you have been feeding him plans this far, isn't it odd that he even HAS a plan to follow suddenly? Wouldn't that make you worried, wouldn't you try to find out WHAT his plan is?

When Teddy is trying to give Lenny clothes in the tattoo place, and Teddy's car's licence plate is being TATTOOED WITH HUGE LETTERS TO HIS THIGH, why doesn't Teddy at least glance at it and recognize his own god damn car's license number?

I mean, pointing back to my first point, wouldn't Teddy be trying to look at everything Lenny has, every new tattoo he's making to figure out what Lenny is trying to do? This makes no sense.

Also, since Teddy has no problems finding Lenny and the Jaguar EACH TIME easily, one time Lenny even CALLS him, why doesn't he take the money out of the trunk at least ONE of those times? He's already seen the money there, he knows exactly what's in the trunk at least the moment Lenny throws the gun on top of the money box in the trunk and closes it. Why doesn't he take the money?

"A car this nice you should lock" - I mean, doesn't Lenny lock the jag every time anyway? I guess he must've forgotten.

Anyway, as soon as Teddy sees Lenny's new thigh tattoo being made (even just a FEW numbers would be enough), why wouldn't he just high tail it out of there and leave this miserable memory guy alone, and live his life on an island somewhere? Why would he just keep following him?

Especially after the whole Dodd-incident (which also makes no sense when you think about it, and how EASY was it to drive some powerful gangster out of town, not plausible), wouldn't Teddy start thinking "too much trouble, the juice is not worth the squeeze anymore", take the money from the jag trunk and leave forever?

I mean, now some 'Dodd' has seen him and can identify him, Lenny is running around with a GUN now, and so on. What sane man would stick around after THAT?

Why does conditioning work on the Sammy-story, but not for at least somewhat recognizing Teddy, even if just instinctually?

Bonus question: WHY would Lenny NOT remember that his own wife is diabetic? THIS makes the least sense in the whole movie. If he remembers everything until the incident, how can be so hazy about this?