This is an interesting thread.,with some good points and I have to say there is more value than instructor seminars for both experienced and inexperienced..
I have always taught for VFR cross country flight planning 1000ft above any obstruction within 5nm of track, so MSA. I would add that includes glider winch cables which are often overlooked as obstructions. It is interesting to note the FAA definition of MSA includes flight over congested in order to glide clear of congested areas. while that is in the UK ANO, I'm not sure if pilots consider that is part of MSA. I should add it is interesting how often ATC in the UK have offered me a VFR clearance below what the FAA would consider MSA for congested areas.
I totally agree with the posts on here that we should teach MSA for VFR and it is beneficial for those going on to IR training and MSA delared at TOC and TOD checks,even in VFR, it is good for SITAW, particularly as airfields such as EGBE no longer give MSA on an arrival from DTY.
Build to add to the above, I would say teach to MSA of VFR cross country flights, but to also teach how to maintain MSA through a 180 turn or to transition down to low level flying, limitations in turning back in valleys, what I call 'flying up a tube'.
Finally, why do we not teach flyht planning to human factors, I can think of nurmerous fatal accidents involving 'getthereitus', it usually involves getting to a wedding, funeral, stag nigh, bussiness meeting, or simply to loose face infront of your PAX.