Hi
@NoWayYesWay, I'm not a native speaker, but here are my thoughts:
The plain dictionary form of a verb like する is used to express an action that will be performed, or is performed regularly:
明日勉強をする I will study tomorrow, or
週末にはテレビを見る I watch TV on the weekends
The 〜ている form is used to express a state of doing the verb being conjugated, AKA the present progressive form:
I am watching TV so please be quiet テレビを見ているから静かにしてください, or
It seems like they still don't understand the reason they got dumped まだ振られた理由が分かっていないようだ。
Of course, they can also both be nominalized and used in different ways to form more complex sentences. We usually run into trouble when we're trying to express a specific grammatical nuance that may bleed over from our native language.
For your examples:
足りる is a bit of a different case because it's not a verb that describes an action with a direct object, it actually describes a state itself (of being "enough," or sufficient). Both of your examples sound fine to me, but 足りない sounds more like a general statement, whereas 足りていない seems more like it's "not enough for the current need."
Similarly, 付き合う also describes the state of going with/dating someone. I think as an English speaker I also tend to overuse the present progressive in cases like this, because in English we might say "the girl I
was dating for two years broke up with me." But in Japanese it is unnecessary; you dated for two years, what point is there to make it present tense, especially when it is now over and your sentence ends in the simple past tense?