re the steering geometry, I think that the logic runs something like this; to avoid toe overlap whilst having a steep head angle ( which supposedly makes the steering better with a front load on) the top tube can end up longer than it might otherwise. This in turn may lead to a shorter stem than might be used otherwise.
I think that you can make a nice bike in CF but that (as well as concerns about damage resistance and repairability etc) it doesn't lend itself so well to many of the design features that folk might want or need on machines of this type. Steel frames can be made infinitely varied in terms of their geometry, and can easily have any conceivable attachment or special fitting added at the whim of the builder/customer. These things can be achieved without a large investment in tooling and so forth.
Unless you are going to start manufacturing carbon forks, most folk start designing a frameset around an available carbon fork, if that is what is to be used. This greatly restricts the range of geometries and fittings that can be used. By contrast you can have whatever you can imagine, more or less, if it is made in steel.
Folk have often said (in a derogatory way) that making steel frames is just 'glorified plumbing'. However in a way, it isn't a bad analogy; no-one in their right mind would start laying up composite material in-situ when (say) installing the pipework in a house, it is much easier to use versatile fittings that can be assembled in any format, modified if necessary.
BTW the drilling near the lower head race appears to be through the head tube wall into the down tube. This part of the head tube isn't so loaded, so removing material at this point (in a lugged and brazed frame) is fair game, if you can be bothered with it. It also helps to ventilate the frame better; I have seen several steel frames that have (after decades) suffered condensation-induced internal corrosion at the top of the down tube. I think this would be less likely with drillings at this point.
BTW bikes that win prizes at shows are very rarely the kinds of bikes that people own and use on a daily basis (in the same way perhaps as you wouldn't wear the crown jewels down the pub, or leave your team Sky replica pinarello locked up outside the supermarket...). They do however show (for good or ill) what can be done; one can admire the craftsmanship and dedication involved, even if the end result leaves you cold, or isn't practical for everyday use.
cheers