Thank you all for the advice!
Although I don't ever ride when it's wet, the improved braking surface is still a plus for me. With my newly attained mass, I'll definitely need all the braking force I can get.
The increased overall wheelset weight is a bummer for sure and looking at the stats, the standard Meilenstein's are 85 grams heavier than the Obermayers and assuming that I've gotten the hub weights right, the breakdown of the difference in weight would be as shown below:
Meilenstein Obermayer: 540g
Meilenstein DT240S Rear Hub: ~209g
Meilenstein Obermayer DT190 Rear Hub: ~183g
Out of the 85g increase in weight over the Obermayers, 26g is due to the difference in hubs. The good news is that this doesn't increase the rotational inertia of the standard Meilenstein's by much since the bulk of the weight in located at the axis of rotation.
The remaining 59 grams however, are spread out across the circumference of the rims thereby increasing the rotational inertia which in turn makes the standard Meilenstein's suffer a bit in terms of acceleration.
The upside however is a pair of wheels that would keep their speed slightly better due to the increased mass.
On top of that, since I'm interested in the 20/20 setup, those extra spokes up front would definitely cause me to suffer as they're no longer as aerodynamic when compared to the 16/20 setup that I'm currently on. However, since I don't intend to race, this seems like a small trade off and with the added confidence that a sturdier wheelset can inspire, I might have to settle with this option.
Another option that I have in mind would be to replace just the front wheel with a 20 spoked Obermayer but I'm not sure what are the weight limits for such a configuration as I can't seem to find any info on them online.