The major factor that influences the equilibrium of this cycle is number of speakers and number of adult learners. Languages with lots of speakers change more slowly, and tend to be getting simpler especially if they are assimilating new speakers (think English as it is becoming the global lingua franca.) Small insular languages with few second language learners tend to get more complex and idiosyncratic.
Source: studied linguistics for a few years.
If history is any indication, in 100 years American English will have some precise ways of expressing things, some loose ways of expressing things, and various groups of people will be unreasonably upset with one situation or the other.
If you're interested in the mechanisms of language change, I found the (2000) 3rd edition of Jean Aitchison's _Language Change: Progress or Decay?_ both readable and worth reading. There is a 4th edition, published in 2013:
http://www.cambridge.org/us/academic/subjects/languages-ling...
And if you don't trust my anecdata, look up the German and Japanese language reform. I don't speak much of those, but they have stronger ruling bodies over their language, making it easier to track change in language. It appears the reforms slowly make the language simpler, based on feedback from the populace.
An explosion of jargon and slang doesn't make a language simple, it adds layers and layers of exclusivity and nuance.
Throw a word like "rotate", and it's just a matter of memorizing what the word means. Throw in a "simple" word like "turn", and it has a gazillion different meanings for every situation. It's a total nightmare for language learners.
'Turn' has many meanings because it has been used too often for reducing the number of words in sentences. You only have two choices when you want to do this: invent a new term (and totally confuse everyone) or use a related term (and let tome of the existing meaning bleed through.) Both of which make the language more complex.
One thing he mentions in the series is that languages tend to become more simple over time as they come into contact with others. This makes sense--if you're bringing people into a community who don't know the language then they're going to simplify it and that will spread. The languages that are the most complex are the ones that are most isolated. Here's a blog post about it: http://lingblog.com/2013/12/23/can-the-structure-of-society-...