Starting at your last sentence, absolutely and I would not try it. That is worst case, adults don't try this in the field. Assuming no Initial drift upwind on boost and coast, the numbers for your flight event sequence goes like this:
Wind speed 29.33 feet/second
Apogee 4000 feet
Main deploy 200 feet
Distance 3800 feet
Drogue Velocity 200 feet/second (!)
Drogue Time 19 seconds
Drogue drift 557 feet
Main deploy 200 feet (!)
Ground 0 feet
Distance 200 feet
Main velocity 15 feet/second
Main time 13.33 second
Main drift 391 feet
Total downwind drift 948 feet
Total upwind drift 0 feet
Total drift 948 feet
I don't know if just having the airframe separated in two halves joined by 25' of shock cord could fly as fast as 200 feet per second, but that is a brutal drogue velocity.
From my assumptions:
Apogee 4000 feet
Main deploy 400 feet
Distance 3600 feet
Drogue Velocity 90 feet/second
Drogue Time 40 second
Drogue drift 1173.33 feet
Main deploy 400 feet
Ground 0 feet
Distance 400 feet
Main velocity 24 feet/second
Main time 16.67 second
Main drift 488.89 feet
Total downwind drift 1662.22 feet
Total upwind drift -785.00 feet
Total drift 877.22 feet
The big difference is accounting for the upwind drift during boost and coast due to weathercocking at such a high wind speed with vmax "only" at around 450 feet/second. I don't know if that is a realistic number but that's what the sim says.
Be that as it may, no way I will launch it on bigger than an "H" without sending a few sounding rockets up to measure time and distance of drift and seeing that it will not be a problem. A custom rockets Galaxy on 12" chute and C11 to start would give the main chute altitude to ground average wind velocity, and D12 and E15 if warranted (and calm enough to recover it!) to get some upper level measurements.