Rav Chaim Kanievsky Shlita (as well as many of the Chassidic Rebbes of the past generations such as the Ruzhiner Rebbe and the Slonimer Rebbe) point out that the first pasuk in Eikev isn't just revealing how to attain bracha from HaShem, rather the pesukim are also an allusion to our avodah to bring Moshiach. The word "Eikev" alludes to our generation, the ikvesa d'meshica. The pasuk is teaching us that if we want to bring Moshiach, our avodah is to be meticulous in all the small mitzvos.
This seemingly needs explanation. What is it about performing small mitzvos that will be the catalyst for the coming of Moshiach? Why does a small miztva make a seemingly more significant impact than a big mitzva?
In order to know the purpose of our generation, we need to know our greatest fault. The Gra in "Ev'en Sh'leima" says that man's sole purpose in creation is to fix himself. Just as this exists on an individual level, it also applies in a more general sense. Every generation of klal Yisrael exists to fix a certain fault, yet in order to know what to fix, we need to know what needs fixing.
As we know, our generation is called the "ikvisa d'meshica", the heel of Moshiach. This isn't telling us that we happen to be on the "heels" of Moshiach, that Moshiach is at our doorstep. It’s a description of our generation. Our essence is likened to a heel. Just like a heel is dead skin and has very little feeling, so too our generation lacks feeling. People walk around every day without any sense of love or fear of HaShem. We've become the numb generation.
With this yesod, the answer to our original question is quite simple. To help bring out the idea, I remember when my wife and I first got married. Everything was so new and exciting. But I remember the thing which flattered my wife the most wasn't the big things. It wasn't running back and forth to the store because she couldn't decide what she wanted. It was remembering the little details. If she would ask me what I thought she would wear, I would say, "how about the black dress you wore on our fourth date?" or something of the sort. It was never the big things. It was always the little details.
Logic should dictate the opposite. It should tell us that the greatest gage of love is when one is willing to go the extra few miles for the loved one. But if we think a little deeper about it, we find that it’s not true. Remembering the big things show that your conscious; remembering all the little details show that you care.
Our greatest fault is that we exist as an Eikev, as a heel. We just don't feel like we should. This is the problem we have to fix. And the only way to start feeling is to start caring about the small stuff.
I think this is the allusion of the pasuk of "V'haya Eikev tishmi'un”. As our Rabbis pointed out, the pasuk alludes to Moshiach. And as Rashi stated, the verse is talking about the small mitzvas which people trample with their feet. Why? Because if you want to be able to feel HaShem's light in all the darkest places, you have to really care about the small things. That's the lesson from the pasuk. It isn't so much a warning for that generation, but it's a counsel for even the lowliest of generations. If we want to feel His presence, we need to care about everything.
The Rema begins the Shulchan Aruch with "Shvisi HaShem L'negdi Tamid". That is, to first and foremost put HaShem in front of us always. And the only way to do this is by learning to feel, by counteracting the yesod of the heel, and in this way we can each do our part to bring the Moshiach.