1. The Midrash reads the word "harim," mountains, in "Esa einai el he'harim" as "horim," parents. As Ya'akov approached the home of Lavan, where he would find his shidduch, he reflected on the fact that Eliezer had made a similar journey at Avraham's behest to find a wife for Yitzchak, his father. However, what a great difference there was between the two journeys! Eliezer had come bearing gifts of gold and jewels. Ya'akov was empty handed. Catching himself thinking such thoughts Ya'akov wondered, "Am I losing my trust in Hashem?" He immediately responded, "Chas v'shalom -- Ezri mei'im Hashem," he trusted in Hashem to make his shidduch ("ezri" hints to a wife, "eizer k'negdo").
The simple reading of the Midrash leads one to believe that Ya'akov was so disheartened by the dire situation in which he found himself that he suffered a momentary crisis of faith. He quickly rallied his bitachon and moved on.
The Chiddushei HaRI"M, however, learns the Midrash differently. It's not possible that Ya'akov Avinu, the "bechir" of the Avos, should have a crisis of faith. Ya'akov's question was rhetorical -- "Am I losing my faith in Hashem?! -- obviously not. Chas v'shalom, such a thing is not impossible. So, wondered Ya'akov, why am I having such thoughts? Why is my mind filled with the notion that I am somehow in desperate straits?
The answer is "Ezri m'im Hashem," these thoughts of despair are only there to raise me to an ever greater level of bitachon and an even deeper appreciation of what trust in Hashem means. Faith that proves itself against challenges and hardship is even deeper and more meaningful than an untested trust.
The focus of the Midrash is not on the development of Ya'akov from a person with doubts (c"v) to a person of greater faith. The focus is on the concept of faith itself, redefining it not as an absence of doubt, but as the ability to overcome doubt.
2. Whether you agree with the Ch. haRI"M's pshat or not, the question that begs asking is why the Midrash needed to introduce the point with the derash on "Esa einai el ha'harim" = "horim." Why not just cut to the chase and say that Ya'akov was worried because he was going to Lavan'm home and did not have a penny in his pocket? He was looking for a shidduch and couldn't even pay for a cup of coffee on a date. What Eliezer brought along when he made the same journey is beside the point.
Apparently the money itself was in fact not Ya'akov's concern. What bothered him more than the fact that he had not a penny -- Hashem could work out a shidduch even if he had no money -- was the fact that he was navigating uncharted waters. He was not following in the footsteps, the "mesorah" of how to make a shidduch, setup by his father and grandfather.