I see iRacing a wee bit different then some. I see it as a long term investment, one that some might think cost alot, but in the long run it really doesn't. I paid for a year right after I got done with beta, and anything less then the one year would have been a bad idea. I know for some it's tough money wise, but I have stopped going out a couple times a month (one or 2 times is like 30 bucks combined minimum IMO). Those 2 times a month, for 4 to 5 months will have me a year of iRacing, and all the other months out of the year I am saving that extra bit of cash on content (that the iR dollars from a year Sub hasn't already paid for).
One thing I wish they would do though is pack each series into a price package. So when you go into D on road and want to drive the skippy, you can get a discounted priced package that pays for the skippy, and all the tracks that are in that series (like 10-20% offEdit: already do this, sorry.). Once you get into higher series, you have most of the tracks already. So then you shouldn't be allowed to get the same discount on those series as when you first entered the skippy series. Catch my drift?
Edit: I forgot that when you buy 3 things at a time it's 10% off, and 6 is 20%. So what I said above can basically be thrown out the window.