[Nexus One Q&A, Help & Troubleshooting] thisisnitwit:
Update #2

So I performed a "clear storage" through the boot loader and was able to seemingly complete the root, however I checked once more using Root Checker and it still told me I was not rooted.

I get the following message from Root Checker:

Root Access is not properly configured or was not granted.

Standard su binary location:

/system/xbin/su: No such file or directory

Alternate su binary location:

/sbin/su: Permission denied

Su binary not found in the system declared PATH

C:\tools>adb devices

List of devices attached

HT9CRP805912 device

C:\tools>adb push GingerBreak /data/local/tmp/GingerBreak

1051 KB/s (0 bytes in 16830.000s)

C:\tools>adb push Superuser.apk /data/local/tmp/Superuser.apk

1023 KB/s (0 bytes in 196521.000s)

C:\tools>adb push busybox /data/local/tmp/busybox

1230 KB/s (0 bytes in 1062992.000s)

C:\tools>adb push su /data/local/tmp/su

820 KB/s (0 bytes in 26264.000s)

C:\tools>adb shell

$ chmod 700

chmod 700

Usage: chmod <MODE> <FILE>

$ chmod 700 /data/local/tmp/GingerBreak

chmod 700 /data/local/tmp/GingerBreak

$ chmod 755 /data/local/tmp/busybox

chmod 755 /data/local/tmp/busybox

$ cd /data/local/tmp

cd /data/local/tmp

$ ./GingerBreak

./GingerBreak

[**] Gingerbreak/Honeybomb -- android 2.[2,3], 3.0 softbreak

[**] (C) 2010-2011 The Android Exploid Crew. All rights reserved.

[**] Kudos to jenzi, the #brownpants-party, the Open Source folks,

[**] Zynamics for ARM skills and Onkel Budi

[**] donate to 7-4-3-C@web.de if you like

[**] Exploit may take a while!

[+] Plain Gingerbread mode!

[+] Found system: 0xafd17ea1 strcmp: 0xafd37b35

[+] Found PT_DYNAMIC of size 232 (29 entries)

[+] Found GOT: 0x00014344

[+] Using device /devices/platform/goldfish_mmc.0

[*] vold: 0063 GOT start: 0x00014344 GOT end: 0x00014384

[*] vold: 0063 idx: -3072 fault addr: 0x00013290

[+] fault address in range (0x00013290,idx=-3072)

[+] Calculated idx: -2003

[*] vold: 1104 idx: -0002003

[*] vold: 1104 idx: -0002002

[*] vold: 1104 idx: -0002001

[*] vold: 1104 idx: -0002000

[*] vold: 1104 idx: -0001999

[*] vold: 1104 idx: -0001998

[*] vold: 1104 idx: -0001997

[*] vold: 1104 idx: -0001996

[*] vold: 1104 idx: -0001995

[*] vold: 1104 idx: -0001994

[!] dance forever my only one

# mount -o remount,rw -t yaffs2 /dev/block/mtdblock3 /system

mount -o remount,rw -t yaffs2 /dev/block/mtdblock3 /system

# chmod 777 /system/bin

chmod 777 /system/bin

# chmod 777 /system/app

chmod 777 /system/app

# cd /data/local/tmp

cd /data/local/tmp

# ./busybox cp busybox /system/bin

./busybox cp busybox /system/bin

# chmod 4755 /system/bin/busybox

chmod 4755 /system/bin/busybox

# busybox cp Superuser.apk /system/app

busybox cp Superuser.apk /system/app

# busybox cp su /system/bin

busybox cp su /system/bin

# chmod 4755 /system/bin/su

chmod 4755 /system/bin/su

# chown root /system/bin/su

chown root /system/bin/su

# chmod 755 /system/bin

chmod 755 /system/bin

# chmod 755 /system/app

chmod 755 /system/app

# mount -o remount,ro -t yaffs2 /dev/block/mtdblock3 /system

mount -o remount,ro -t yaffs2 /dev/block/mtdblock3 /system

# exit

exit

$ exit

exit

C:\tools>