Hi JenTay,

I believe that your car, like my 86 SDL, has a shift 'softener' which applies more vacuum to the vacuum modulator when the engine is cold, thereby making the shift softer.

It's possible that the modulator is giving overall shifts that are too soft, and it's most noticeable when cold, or that the vacuum valve is applying too much vacuum at a given pedal travel.

Mine flares pretty dramatically for the first 3 or 4 shifts when cold, then settles down.

By all means change the trans fluid, and figure if it's still too soft when the engine is cold, it might need some other adjustments.

Best Regards,
Jim