PC Doc Pro is about $30, and is more or less the equal of any of the "One-Click-Fix-Kits"; nothing much to look at there. Most of 'em are reasonably safe, none are very effective. Spybot S&D's "System Internals" feature and CCleaner's "Issues" feature will more or less do whatever any of the paid "Fixer-uppers" can do, and they're free.
The free-for-personal-use version of SiSoftware's excellent
SANDRA (
System
ANalyser,
Diagnostic and
Reporting
Assistant) is a versatile, thorough system-analysis tool, and will provide you with a tremendous amount of information about your machine, your system, and what's going on there.
Boot problems typically stem from a bad or missing service or driver, or an incorrect call for one. A boot log is the way to go to see what boots when, and whether it offers any problems.
See About.com:
Boot Log
For more detail and tips, see:
Microsoft:
How To Troubleshoot Startup Problems in Windows 2000
Microsoft:
How To Diagnose System Problems with Event Viewer in Microsoft Windows 2000