I don't know. I run into this problem myself.
On the one hand is my collection of parts. Removed from equipment, retrieved from dumpsters, picked up via eBay, surplus shops, sample programs, excess inventory, etc. Years of loving hoarding, extensive stock of classic parts; I could build ... so much stuff.
On the other hand, is Moore's law, and the current state-of-the-art in processors, evaluation boards, and hobby electronics. Even at $25/month, you can quickly build up a stock of modern systems with no hacking required to get going. Except that hacking was sort-of part of the goal in the first place.
I would encourage you to get at least one piece of "it just runs" equipment, whether that's a TI LaunchPad,
a full-priced Arduino, or a commercial respected AVR programmer. Once upon a time, I wrote a simulator for the 8085 processor. And an assembler. And I typed in a Forth implementation from a magazine, ran it through my assembler, and loaded it up on the simulator. Where it did NOT work, leaving me very frustrated with the fact that I didn't know which piece(s) of self-developed error-prone code was broken.
You owe it to yourself to avoid whatever frustrations would be most frustrating an least fun to deal with, even if that means saving your "hack money" for a couple of months.
Perhaps this is why Arduino is so successful; in the end you can plug it in and load the examples, convincing yourself that SOMETHING is working. The flip side is all those people claiming to use Arduino, when pretty much all they've really done is loaded the examples...
TI has recently done some pretty nice, and VERY COMPLETE "web workshop" tutorials for their launchpad boards. They're a bit ironic compared to Arduino/etc, but they seem to specifically address some of the "start-up issues" ("I need how many tools, from where?") and delve pretty quickly into "real" microcomputer programming. MSP430 here:
http://processors.wiki.ti.com/index.php/Getting_Started_with_the_MSP430_LaunchPad_WorkshopStellaris here:
http://processors.wiki.ti.com/index.php/Getting_Started_with_the_Stellaris_EK-LM4F120XL_LaunchPad_Workshop?DCMP=Stellaris&HQS=StellarisLaunchPadWorkshop