We must surrender everything to God's Sovereignty -- even the date of the Rapture. Time and again, we are each hurt by a "high watch date" that comes and goes. The fault is not in God, but in man. Therefore, all we can do is know the season...and wait.
I'm sure you'll agree we are in the season. Whether Yeshua returns in 5 minutes or 5 years, it remains the season of His coming. The signs of the times are proof of that.
But God told me recently that relationship with Him is first and foremost. His coming is secondary. That might shock a few, but it's true, actually. If you spend your time abiding in Yeshua, TRULY abiding in Him, you will be ready for His coming regardless of the actual date.
And even if He tarries and you live your life and die an old, old man, it is not a life wasted to be watching the skies for our Lord. Living the abiding life is living the abundant life, brother. It is not folly to always be prepared, because we DON'T know. The side effect of "being ready" is that you live a holy life as Christ's true disciple and not a worldly Christian.
Yeshua told us to occupy. Therefore, He doesn't want us to sit on our backsides on the porch just waitin'. If we're waiting, we're not working, amen? So yes, make your plans, buy your groceries, go on vacation, keep saving your money, propose to your girlfriend, paint your house... Keep doing those things. Even if Christ comes tomorrow, it is not "wasted" to make plans.
Another thing I've learned from the Holy Spirit is the fact that my salvation is SECURE. Nothing and no one on this earth can take me out of my Savior's hands. So whether He comes in 5 minutes or 5 years, it matters not, because the end goal remains the same -- I'm going to HEAVEN!!
If we're still in this world, then we still have work to do. We're still "needed" in our area of the Body of Christ. If you had no more work to do, God would call you home. Therefore, I see Christ tarrying as an opportunity to: A.) gain more heavenly treasure & B.) to become more like Him.
I believe once we get to Heaven, certain lessons can no longer be taught by experience, because there is no pain or suffering in Heaven. There's nothing up there that can teach us total dependence on God because we're in a perfect place and we'll know Him face-to-face. Therefore, the events that shape us here on earth, mold us into the people Yeshua wants to rule and reign in His Kingdom.
And if He's not finished molding me into that person, then I have to stay in the temporal, because I cannot experience it in Heaven. Does that make sense?
Anyhow, be at peace, brother. Don't let the Rapture, or any failed dates, consume you. Rest in knowing that your inheritance in Christ is secure, and at the end of the day, your destination is the same. And whether or not you die in this world or are carried away alive on God's Whirlwind, you WILL be present at the Rapture. It matters not whether we're asleep or awake in Christ on the day of His coming, the Body of Christ shall be glorified. (Aside from the cool story of never dying you might have in Heaven :P)
Whom have I in heaven but You? And there is nothing on earth that I desire besides You. My flesh and my heart may fail, but God is the strength of my heart and my portion forever. ~~Psalm 73:25-26 (ESV)