Exodus 16:1 would suggest 'let down' to Israel. To appreciate what Wilderness meant to Israel we need to have some idea what land meant to them. Walter Brueggemann's 'The Land' is a terrific study on that major OT theme. 'Land' is the place of blessing, it's where God is present and where fellowship with him is assured, it's home, security, it's the proof that things are OK between God and the people. It stands over against 'wilderness' as 'blessing' stands over against 'curse'.
In Genesis 1 God gives form to formlessness, life to lifelessness, harmony to chaos (at least from a human habitation point of view). Everything had its place and 'cooperated' with the other elements. The sun and moon were where they should be doing what they were supposed to do, the birds were in the air, the fish in the sea, there was life, swarming, teeming, abundant life and it was all pronounced 'good', even 'very good'.
With Sin came 'curse' and with curse, death, disharmony, conflict, distrust, the violation of appointed places. Curse was 'uncreation'. The water returned over the land and covered it, life died rather than burst forth, disruption spread, sweat, thorns, thistles, back-breaking toilall this entered.
Nothing showed 'curse' so vividly as Wilderness. Homelessness was never so clearly brought home. The absence of blessing was glaring and with the absence of blessing, the absence of God was deduced. Blessing was only possible in land that could be tilled or sowed (cf. Jeremiah 2:2) so wilderness, wasteland, was a visible reminder of curse, a visible reminder of the gulf between God and Man. To be driven from land (cf. Adam, Eve, Cain, or Israel in exile) was a horrific experience for those who had this conception of land.
Suppose we're on a high place overlooking the wildernesses in the Sinai peninsula and we're panning it with our binoculars. As far as the eyes can see there is barrenness, stunted growth, waterless land, lower life-forms, pitiless heat, erratic boulders, a struggle for survival, scorpions and serpents, dust and the weary wind. Then down below us, suddenly, we're met by a profusion of color and life. Tents pitched in thousands, all in order and placed with precision around a central Tent. We see herds of goats, flocks of sheep, we strain our ears and the wind carries the sound of laughter up to us, a joyous shout now and then rises to us or the sound of music. How's this possible? Is it a mirage? Here! In the middle of all this absence of promise there is life, real life, flourishing, thriving life. How did they get here? How do they sustain themselves? In the midst of curse there is this blessing? In this chaos could we expect this order and harmony?
Israel's experience in the wilderness was to be remembered for all their generations. Yahweh established the Feast of Booths (Tabernacles) so that they would never forget the time when God guided them through the trackless desert (Deuteronomy 8:15), and spread a table for them in that inhospitable land (Psalm 68:8-10; 78:18-30). It was a test for them, of course (Deuteronomy 8:2ff) and God wanted them to grow in their trust of him through and by means of the testing.
What he wanted was for them to respond nobly, gallantly, but the Wilderness became a token of their unbelief, their bitter complaining because freedom involved pain and very often they preferred slavery if it was dished up with onions and leeks to freedom if it involved a tough pilgrimage.
Israel's Messiah, Jesus of Nazareth, came to represent Israel (and consequently, humanity at large) and endured a Wilderness experience (Matt 4 and parallels). In the Wilderness he did all that Israel was supposed to do and didn't. He rejected the temptation to bitterly demand bread since (or if) he was God's Son, he rejected Satan as the god who would go before him and bring him into the kingdom and he humbly submitted to the experience rather than tempt God for proof that he was there with him in the Wilderness. Centuries earlier the Tempter had met Israel in the wilderness and brought it to its knees but by the grace of God, the elect survived and the Evil One met 'Israel' again and lost. What the Messiah did in the Wilderness was what Yahweh wanted from the nation.
For Israel the Wilderness became, though it did not have to be, a time of punishment and judgement. Numbers 14:34 speaks God's judgement on distrust and Israel is divided into two groups. 'Wanderers' who are going nowhere and 'pilgrims' who are going somewhere, even if takes a while getting where they are going. The NT bears witness to this punishment element in Israel's Wilderness experience Hebrews 3:4.
And although many Israelites didn't believe it, the wilderness spoke of freedom. It isn't possible to understand the Wilderness experience of Israel without the Exodus as prologue and settlement in Canaan as epilogue. How did they get there (and where were they going)? However harsh and without promise the Wilderness was, it was 'out of Egypt'. It may have been away from cucumbers, leeks, garlic and flesh-pots but it was also away from slavers, murderous overlords, seven-day-schedules that ran from morn till night.
It may have been a brutal environment for the body but for the heart and soul, for Israel's heart and soul, it was another realm. The sun rose on free men, women and children (who were going home).
For some who say yes to God in Christ, life becomes harder, there are more pressures, there's more pain but it's still a different world. They've been freed from the Evil Prince who enslaved them and to whom they had enslaved themselves. The very pressures now on them as disciples of Christ are a token of their freedom, their salvation (Philippians 1:28-29).