Mark, keep in mind this is a diocesan TLM if there is one on a Saturday.  Therefore, it might not be a doctrinal pull, but a liturgical pull.  I'll give him the benefit of the doubt at this point.

I gave the benefit of the doubt with the first (original) post, but the follow-up post quoting chapter and verse of the Novus Ordo "Canon law" [vomiting] is not the mark of the innocently ignorant.

I was born and raised in novus Ordo. 

As I interpreted the OP’s question, it wasn’t about “anticipated Masses” but whether a single Mass could fulfill BOTH the Sunday AND the Holy Day obligation.  The answer is no, one Mass attendance is required for EACH obligation.  If a suitable Mass is not available, if one is sick, if one has to work, if it’s just not possible to attend a Mass of obligation for a legitimate reason, than the obligation is dispensed, it is not satisfied by “another Mass at another time”.  With that said, it’s not a bad thing to attend a daily Mass if one wasn’t able to assist at a Sunday or Holy Day Mass for a legitimate reason, but one is doing so to worship God and receive grace, NOT to fulfill the prior missed obligation.
 
I’m not sure how things wandered off into the “anticipated Mass” territory and I don’t have a comment to make about those.  However, it is interesting to observe that many traditionalist attend Mass on Sunday afternoon or evening, and those may be the only Mass times available to them.  These were forbidden times for Mass until Pope Pius XII permitted them in the early 1950’s when Msgr. Annibale Bugnini was Secretary to the Papal Commission for Liturgical Reform.  Previously, other than Midnight Mass at Christmas, Mass was only celebrated between dawn and noon.  In the 19^th century there were indults given for Mass to be said before dawn, but these were for special reasons, not general use.  This was also when the tradition of fasting from midnight before receiving Holy Communion was reduced to just three hours.

I had to choose this year whether to attend Mass today, Sunday, or tomorrow, Christmas.  It’s a three hour drive and I’m just beyond the point, health wise, of spending two nights “sleeping” in my car during winter. Motels are all booked and too expensive.  Driving six hours two days in a row with Mass in between isn’t reasonable, either.  12 hours behind the wheel in 48 hours leaves time for what, a short rest at home before repeating it?  Not to mention the price of gas in Canada is ridiculous!  So I prayed online Mass at home this morning.  I’ll be off by 5:30 tomorrow morning for Christmas Mass at 10:00, Confessions at 9:15.  I don’t know what is the rule about being dispensed, but 158 miles probably qualifies.  

Merry and Blessed Christmas to All!  🌴 🌟 🧚🏾‍♂️🐑🧔🏽‍♀️🤱🐮🐴🐂🌴           🚶🏻‍♂️  🐫 🐫 🐫 🐫 🐫 

It would be 300 mi round trip for me.  However because of my recent spine surgery I can't drive that distance anyway. We will be celebrating Christmas at home.

That’s about the same distance for Mass, but having recent back surgery doesn’t need a special dispensation.  Illness, injury, or near or literal impossibility automatically dispenses one from Mass. Just be sure to observe the day as holy.  For now, most of us can watch Mass on line from home recorded or live-streamed.  If not, there’s always the Missal readings and one can pray the Rosary.  

Not sure where I learned this, but I thought I heard that there is no obligation if more than an hour one way.