I actually agree with SupraBlur... waiting till you're 50 (lol, I'm that this year) and then looking back and saying "why didn't I do this sooner!"
In retrospect, yeah, hind-sight is 20/20, look at the big picture. A house is going to be a long term comittment. At least 30 years. If you buy entry level, then sell for a profit and dump into an upgrade, and so forth, your house buying is essentially a life long pursuit, assuming you join the rat race (work with regular pay raises, good investing, living within your means, etc.)
As you're witnessing, housing goes into cycles of lows, then highs, then "higher", then lows, then repeats.
When I bough my house in 91', it was STILL going down from it's lofty 340K to a bottom of 309K! I bought in at 319K not knowing. Today, I can sell it for over $800K, possibly $900K.
You're in a pickle because this IS the best time to get into a house while it's still "relatively" low. I guarantee you it'll pick up again in about 5 years. But step away from the forrest.... like I said before, a house is really a life long journey.
So knowing what I know today, if I could go back in time, instead of that GTI I bought, I think I would of rather of bought an M3 in 86' or a Porsche 944 Turbo! So I'm eating $0.10 Top Ramen and PBJ for a year.... I know I would have been much happier and STILL have a home.
But that's me. I'm that 50 year old with the two cars in my Avatar (HAH, I got them BEFORE I turned 50!!!).
PS: might be asking "so why the A5"? to be honest, I didn't want the high HP sedan because my wife would be driving it. She insists I drive faster than her but my kids never lie; she drives faster than me!!!! My speed fix is the Cobra at over 400hp so I didn't need it in the A5. And fortunately, the dealership didn't have an S5 to test; it might of been a different story! ;D