Excellent advice. Take it from someone who’s been praying the hours for decades.
Yep! Though I prefer Holy Week, the Triduum, and the Octave of Easter to Christmas season. At least the Octave of Easter is stable. The Octave of Christmas has all sorts of feasts intermingled, then there’s time before and after Epiphany, and it’s all compressed into a short period with no breathing room. I’ve been praying the LOTH for over 10 years myself and still Christmas throws me for a loop… even more so because I chant the Offices in Latin Gregorian chant.
The Triduum is actually pretty easy if you follow Monastic practice: there’s no opening verse, no hymn, the responsory is replaced by the gradual “Christus factus est…” (though that’s no picnic to sing, but our schola has been doing it for a few years so one can muddle through) and no concluding rites. The only major issue is that there are proper antiphons all week, but if you read the Office that’s not an issue.
Also during the Triduum, if you attend Holy Thursday Mass and the Good Friday liturgies, you’re exempt from Vespers on those days, and from Compline if you attend the Easter Vigil.
Still, as our prior says “I have a great devotion to St. Feria”

and Ordinary Time is probably the best place to start, though Lent is, I think, even easier as there are so few feasts and no memorials.