了 as le or liǎo, too.
Did it get more numerous with the adoption of simplified characters?
I'm not sure, but I believe that most, if not all, mergers from simplification were homophones.
Yes, it did if you're not a mandarin speaker. The simplification process was biased towards Mandarin and there are some words that were merged that have different pronunciations in Cantonese but not in Mandarin.
* 行: xíng or háng
* 的: de or dì
* 长: cháng or zhǎng
(plus I'm sure many more that I can't think of just right now)