It may depend on the context but I understand each sentence like the below ： 文脈によって変わるかもしれませんが、私はそれぞれの文章を以下のように理解します。 (1) 毎日食べようとしている I try to eat something every day. (2) 毎日食べるようにしている I make it a habit to eat something every day. Sorry for my poor English.

Hey Nathan, good question. I'll take a shot at it. Volitional form expresses intention/will. You can use volitional + と思う to express that you've decided to (verb). Following this usage, I believe volitional + とする expresses that you will do the verb or している that you are currently doing it. Simple form verb + ようにする means "try to (verb)" or している "trying to do (verb)". So I think the difference between the two is that ようにする expresses more indecisiveness whereas とする expresses more will/intention/certainty. Now here's my attempt at a translation of the two sentences. Number 2 is much easier to translate than number 1. 1) I've gone with eating every day. (strange English but sometimes Japanese just doesn't translate well into English) 2) I'm trying to eat every day.