Hi John,
I know exactly what you mean.
Do you know that when the Hebrews left Egypt in the exodus, they brought their Egyptian relatives with them, and their idols? Not to mention [i]making[/i] a golden calf as well? You know what happened in the wilderness. If not, read Exodus, and see just how extreme a time God engineers, that they may be totally dependent on Him.
From His point of view, He brought them into the wilderness to rest (from their bondage), and to worship Him. In fact, Exo 19 - He says He bare them on eagles' wings 'unto myself'. That's where they became a peculiar people, a holy nation, a royal priesthood - in the making - if, they would obey Him.
Then there is the question of whether you're prepared to cross Jordan in flood, at the time of the barley harvest, to enter the promised land.
They really [i]knew[/i] they had been delivered, as they looked back across Jordan, by the time they won their first battle. They had left the wilderness behind, but a new enemy confronted them, trying to prevent them from possessing the land God had given them. Note, God was using them to get rid of those who had always opposed Him. Interesting. Just like our inbred sin.