It's not regional (except insofar as it seems to me to be more AmE than
BrE) and not sloppy, in my opinion -- unless you want to say also that
British speakers who say "choon" for "tune" are sloppy.
It is "glide absorption", and it is the
sine qua non of authentic American pronunciation.
Non-natives in the U.S. who cannot master this (and the intervocallic
"t" as "d" when necessary) never sound as though they have an adequate
command of American English, chiefly because everything they say sounds
so excessively precise and measured, so inexperienced, so learned out
of a book.
However, glide absorption is applied by natives preferentially to
common groupings involving the forms of the pronoun "you" and to
groupings with "year" ("next year", "last year" with the "ch" sound).
For place names like Old York Road it is up to the local inhabitants to
decide!
Note that word
internal interfaces between the same consonant families form a case of
required
glide absorption. "picture", for example, cannot be said "pikt- yoor"
in American English without eliciting a raised eyebrow or two. The
same can be said for "soldier" said as "sold-yer" or "pressure" as
"press- yoor", or "precious" as "press- yuss" and so on. It just
happens that
between words, the same combinations can occur,
and there the tendency of speakers is to use the same phonetic
transformations as within words. Between words glide absorption may be
optional, but it is certainly not forbidden.
CJ