Torque convertor and detonation

Folks,
I have been chasing timing issues with my motor and have come to the revelation that my torque convertor might be the real problem. Here's the background info.

Mild 360 low-comp build, smog heads and XE 262 cam, eddy intake and performer 500cfm carb, full tti exhaust, factory distributor with pertronix. Factory stall convertor (2k?) with 3.23 gears in 727.

Ray (halifaxhops) curved the dizzy for me, I forget the specs offhand but it is somewhere around 12*/24* mechanical, all in around 2500. I can run around 15* initial, 39* mechanical on 91 octane and the car runs like a raped ape. But to dial it back for 87, I have to pull it back to like 10* initial, 34* mech or I get detonation at 2k under load.
So all that makes sense, and before you say, no **** Sherlock, if you want to run pump gas you have to retard the timing... here's my thought, the motor really runs good with the more advanced settings on 87 octane (ideally 15/39*) it only detonates at around 2k-2200 rpm, which is right where the stall convertor puts it under initial load.

So here's my thought, I can either mess around with springs in the dizzy and get timing to come in later, OR, should I stop chasing my tail and get a higher stall convertor? Am I giving up a lot of grunt and fun ripping around on the street (this is a stoplight to stoplight car, no racing) with that factory stall convertor?

Before you respond, understand that

1) I daily drive this car, it will never race or get dyon'ed, I just want it to run really well and have very responsive throttle
2) I intentionally built a low-compression motor to be bulletproof and be able to run 87 octane and still have some grunt, so adding octane is not really an option

What do the pro's think, stick with my stock stall convertor and just adapt the timing curve, or is it worth the $$ and effort to replace that stall convertor... will it alleviate my detonation issue, dramatically increase acceleration? Car does 6.5 sec 0-60 consistently just mashing the pedal in D, no launch.