Highlands and Lowlands

On leafing through LPD3, I came across the word Highland and I noticed that Professor Wells syllabifies it as ˈhaɪl.ənd. I then checked the term Lowland and saw it was syllabified as ˈləʊ.lənd. So I wondered: why is that? Do native speakers of English really pronounce these words in slightly different ways? Does it depend on the origins of each term?

If you check in Roach et al. (2006)'s CPD, both words appear as -.lənd, which indicates that in the authors' mental lexicon the words Highland and Lowland are probably analysed as a combination of high/low + land. Not so in LPD, in which the syllabic division proposed by John Wells is not evident from the orthography or from the morphology.
The difference between ˈhaɪl.ənd and ˈhaɪ.lənd lies in the l phoneme. Phonetically, in fact, the first l, being in syllable-final pre-vocalic position, is shorter and weaker than the second l, which is longer and stronger being in syllable-initial position.
Although I was aware of the fact that the LPD's syllabification principles are somewhat different from the ones adopted in CPD, I dared ask Professor Wells why he thought that Highland should be syllabified as ˈhaɪl.ənd and Lowland as ˈləʊ.lənd, to which he kindly answered:

This is not based on any theoretical considerations, just on my intuitions on how I say them and how most people seem to say them.
Compare highly.

Fascinating, isn't it?

If you want to know more about Professor Wells's syllabification principles, read here.