Do languages get simpler over time?

I’ve noticed trends in languages where they seem to get “simpler” both in terms of pronunciation and in terms of grammar.

A lot of people complain that English is “degenerating” and such, and while I don’t necessarily think that, it is true that grammatically the language seems to have simplified. For example, only one verb inflection ending for present tense remains: ”-s” to mean 3rd person singular as in “sings”, “takes”, “wins”, “does”, etc. English used to have more, like “taketh”, “takest”, etc. The subjunctive is also disappearing and words like “whence” and “thither” went away in favor of just “where” and “there” and the word “whom” is disappearing from usage as well. Noun declensions also tend to disappear over time.

Modern Greek took most of its diphthongs like “oi”, “ei”, that were originally pronounced “oh-ee” and “eh-ee” (said quickly) and they are now both pronounced just “ee”. Likewise, the vowel upsilon was pronounced like the French “u” and now it is pronounced “ee”.

How much simpler do you think English will become? Do you have any other examples of languages doing this? Why does this happen? Is it always for convenience? There are some instances where I think such “simplifications” actually make the language more ambiguous.