Coach Koulouf!
Great suggestions my friend. As well as developing better proficiency in the BASt, I think this guy should probably ensure their HSPU is consistent on the floor, before "plugging in" to this integration (luckily, there are some new progressive-HSPU resources coming soon to the VRL ;) )
R.e. low-volume practice of the 'L-sit to Press HS', the idea makes sense for "polishing" the integration, however I feel there is something LACKING in this practitioner's capacities which would make that "polishing" more productive - namely, development of FRONT-FOLD range and COMPRESSION. This will really help him a lot to make the movement more mechanically advantageous. He clearly has a good base of SAS pressing strength, but active mobility is not really up to the same level. Investing a lot in this, maybe 2-4 phases of 6-8 weeks practice with "hard focus" could already make a big difference, and maybe the latter phase/s then incorporating the low-volume integration.
The distinction between a rep & attempt is a really nice consideration - this will certainly help him take a step back from the perspective of "try and try and try until you get it", which generally has very poor results! If he is so eager, however, having "attempts" opens up na opportunity to still express the movement he is clearly very excited to achieve so he can better answer the question "where am I", whilst still keeping a solid base of "clean" repetition & practice consistent in the background.
Thank you for the advice my friend!