The Circuitous Route and Reclining
One source for the requirement that we recline at the Seder as we eat the Matzah and drink the Four Cups of Wine is derived by the Midrash from this week’s parsha.
“G‑d led the people on a roundabout route [Vayaseiv] through the desert….”
The Midrash states:
From here our Sages [Mishnah, Pesachim 10:1] taught: Even the poorest in Israel may not eat unless he reclines, for so did the Holy One, Blessed is He, do for them, for it states, ”Vayaseiv Elokim – G‑d led them through a roundabout way.” [The word for roundabout is similar to reclining.]
What does the idea of reclining at the Seder have in common with the Jewish people being led by G‑d on a circuitous route?
Second, conventional wisdom is that we recline as an expression of freedom and aristocratic wealth. One would have thought that a poor person should not adopt a ritual that belies his true status. The Mishnah therefore comes to tell us that even a poor person must recline because, in truth, every Jew must feel the power of liberation on the night of the Seder. On that night we are all rich aristocrats because our G‑dly soul is indeed free and rich. Our external actions must reflect the inner truth rather than some superficial reality.
However, this explanation makes sense only when the requirement of reclining is seen as an expression of freedom and wealth. But the Midrash seems to suggest that our reclining is based on the circular path we took from Egypt to Israel. If so, one is entitled to ask, what difference would it make if the person was rich or poor?
Bread of Affliction
One may suggest the following explanation, based on a discourse of the Rebbe on the Haggadah where he cites its introductory paragraph:
This is the bread of affliction that our fathers ate in the land of Egypt. Whoever is hungry, let him come and eat; whoever is in need, let him come and conduct [the Seder of] Passover. This year [we are] here; next year in the Land of Israel. This year [we are] slaves; next year [we will be] free people.
Even a cursory examination of this introductory paragraph raises several questions: 
First, why was this paragraph chosen to introduce the Haggadah when it doesn’t really describe the Exodus? Instead it speaks of the Matzah we ate when we were slaves in Egypt?
Second, this reason for eating Matzah contradicts a later statement, taken from the Torah, that we eat Matzah because G‑d took us out of the Egypt in haste and we had no time to allow the dough to rise so we had to bake Matzah.
Third, what is the connection between the statement about the Matzah we ate in Egypt and the invitation to the poor and needy to join us?
Fourth, how can we extend an invitation to the poor when we are already in midst of the Seder, comfortably ensconced in our own cozy homes and “secure” that no poor person on the outside will ever hear our invitation? We must conclude that the invitations must have gone out earlier in the day. If so, why are we repeating the invitation now?
A Pressing Question
The Rebbe answers all these questions by establishing that this paragraph is actually a response to a pressing question that arises as soon as we start the Seder. And, unless answered, it will not allow a thinking person to continue the Seder.
The pressing question is: If G‑d is perfect and true, then His actions are perfect and enduring. So why is that we are back in Galus? And why is it that there are still Jews suffering from poverty if G‑d promised that they would all emerge from Egypt with great wealth? How could G‑d’s purposes not be sustained?
The Rebbe’s answer is that even as we left Egypt, we carried with us our bread of affliction, our spiritual poverty. From the very outset, the Exodus was not complete. This explains why it is still possible that we are still in exile and need to invite poor people into our homes to join our celebration of Passover.
The Long Route to Freedom and Wealth
If we follow the above premise it can also explain why G‑d had to take the Jews through a circuitous route to the Land of Israel. Going straight into Israel and experiencing a struggle with hostile moral forces while handicapped by their impoverished, “bread of affliction,” state of mind, would have caused a major relapse, perhaps even back into bondage.
Hence the Mishnah and Midrash state that that even a poor person must recline. Notwithstanding the existence of poverty, physical or spiritual, we still have the power to unleash the Geulah dynamic.
The fact that poverty exists suggests that the experience of the Exodus was not fully internalized and we are not truly free. Thus, one would have thought that the poor should not engage in a spiritually affluent exercise. The Midrash therefore makes it clear that the poor must recline because to do so relates to the circuitous route out of Egypt that was taken for the benefit of the impoverished Jew so that he or she too can finally get out of Galus and its impoverished state of affairs.
The Rebbe explains that by engaging in the Seder, eating the Matzah, etc., we provide ourselves with the ability to get out of Galus, once and for all! No Jew should ever consider himself or herself beyond Redemption. As the Rebbe stated repeatedly, “No Jew will be left behind.” Every Jew will eventually discover the riches and freedom that have eluded him or her for so long.
Reclining has a dual function. For some it is an expression of their spiritual wealth and freedom. For those who are spiritually poor it shows them the circuitous road to Redemption that will lead them inexorably to the same destination. 
Moshiach: The Poor-Rich Man
One may suggest another approach to this requirement for the poor person to recline despite his impoverishment.
Moshiach is described by the prophet Zecharya as: “a poor person riding on a donkey.” The Talmud (Sanhedrin) contrasts this impoverished arrival, with the Book of Daniel where Moshiach is depicted as, “appearing on a heavenly cloud.” The Talmud explains that these two scenarios reflect the possible state of the Jewish people at the time of Moshiach’s arrival. If the people are underserving so that Redemption will occur in its prescribed time, Moshiach will come in a natural manner without fanfare and miracles. If we are particularly deserving so the Redemption is hastened, Moshiach’s coming will be spectacular, rich and supernatural.
We may suggest here that when our Sages discuss the need for a poor person to recline, they may also be alluding to Moshiach himself. [The commentary Or Hachaim explains that when the Torah speaks of a poor man it is an allusion to Moshiach, who is in a state of suffering and pain because of the pain and suffering we endure every additional minute we languish in Galus.]
Not only does the spiritually rich and majestic Moshiach, who arrives on a cloud, have to recline, but even when Moshiach’s coming is natural and impoverished, he still needs to exude a sense of freedom and wealth by reclining.
On the contrary, explains Rabbi Dovber of Lubavitch (known as the Mitteler Rebbe, the son of Rabbi Schneur Zalman of Liadi the founder of the Chabad movement)!  He explains in his work Sha’arei Orah that there is an advantage to Moshiach coming in his prescribed time rather than in an accelerated mode, because it suggests that we have successfully refined all the hidden sparks of holiness.  If Moshiach comes before the designated time, there might be some sparks of holiness that were overlooked and left languishing. Moreover, the Rebbe explains (Toras Menachem volume 33 p. 331), the length of our Galus has also given us time to discover incredible treasures of Torah knowledge. Had the Redemption been accelerated we would have missed those anticipatory revelations of Divine knowledge.
This, then, can be the meaning of G‑d taking the Jews through the circuitous route as the source of our need to recline. What, we may ask, in the connection between a circuitous route and a sign of wealth and freedom?
The answer is that although the winding route was needed for the process of refinement to get rid of the Egyptian negativity, taking the roundabout path would guarantee that the Children of Israel were truly and successfully liberated. That would lead to even greater wealth in the long run.
So, here is the paradox. If the Redemption occurs in its time, that suggests  we have remained in an impoverished state and Moshiach must ride on a donkey. On the other hand, it also suggests that we have accumulated that which we needed to have before Moshiach’s coming.  As a consequence, we enter into Eretz Yisroel with all the wealth that was harvested through our long and arduous exile. Although we may be poor in the context of our present state of affairs, we arrive with a very hefty “savings account.”
Conversely, when Moshiach’s arrival is accelerated, it is because we are a spiritually rich generation, but collectively we may not have accumulated as much.
Thus, our Sages state that while we prefer Moshiach’s accelerated arrival in a state of wealth, there is another scenario that is equally an expression of wealth, even if it seems to reflect a state of poverty. Even if we have finally arrived at the due date for Moshiach we have to know that, regardless of our present status, we are indeed spiritually wealthy because of our cumulative wealth, and we must demonstrate that state of affluence by reclining at the Seder.
The Best of Both Worlds
From the Rebbe’s many declarations it seems that the ideal situation will be for us is to have a combination of “in its time” and “hastened.” This way we will have the best of both worlds. First, we have a hefty spiritual “savings account” due to our prolonged stay in exile. In addition, we have more than ample liquidity.
Our generation, despite all physical and spiritual obstacles, has displayed incredible sacrifice and dedication to G‑d and His Torah. So, we have a double claim to reclining; one for our winding, arduous and circuitous journey through Galus, where we picked up untold wealth. And the other, for the wealth that our own generation has independently generated. We are certainly more than ready for Redemption!