Time Machine does not cope well with nearly-full disk

Although Time Machine is supposed to delete old backups when the disk fills up, under some circumstances it does not cope well with a disk-full condition.
Hardware: iMac (mid 2007)
OS: Mac OS X version 10.6.8 (Snow Leopard)
Processor: 2.8 GHz Intel Core 2 Duo
Memory: 2 GB 667 MHz DDR2 SDRAM
The other day I noticed that I had not had a successful Time Machine backup in over a day. Backups were taking a long time to run (4 hours or more), during which time the backup disk was chattering constantly and the disk showed "Estimating index time" in the Spotlight menu (even though I had excluded the disk from Spotlight indexing). When the disk finally stopped chattering, the backup finished with no visible errors but Time Machine continued to state that the last successful backup was yesterday. The backup disk was nearly full, but I had assumed that Time Machine was designed to cope with this situation by deleting old backups.
A complete annotated log file of the incident and my observations can be found here: http://bentopress.com/backup.log.zip
Here are some of the interesting entries from the system.log file:
Sep 7 16:22:14 Bento-iMac com.apple.backupd[56515]: Starting standard backup
Sep 7 16:22:14 Bento-iMac com.apple.backupd[56515]: Backing up to: /Volumes/My Backup Disk/Backups.backupdb
Sep 7 16:23:07 Bento-iMac com.apple.backupd[56515]: No pre-backup thinning needed: 100.0 MB requested (including padding), 137.2 MB available
Sep 7 16:25:49 Bento-iMac com.apple.backupd[56515]: Copied 32984 files (23.7 MB) from volume iMac HD.
Sep 7 16:25:53 Bento-iMac com.apple.backupd[56515]: No pre-backup thinning needed: 100.0 MB requested (including padding), 108.4 MB available
Sep 7 16:25:57 Bento-iMac KernelEventAgent[47]: tid 00000000 type 'hfs', mounted on '/Volumes/My Backup Disk', from '/dev/disk1s3', low disk, very low disk
Sep 7 16:25:58 Bento-iMac mds[45]: (Normal) DiskStore: Rebuilding index for /Volumes/My Backup Disk/Backups.backupdb
Sep 7 16:25:58 Bento-iMac KernelEventAgent[47]: tid 00000000 type 'hfs', mounted on '/Volumes/My Backup Disk', from '/dev/disk1s3', low disk
Sep 7 16:25:59 Bento-iMac mds[45]: (Normal) DiskStore: Creating index for /Volumes/My Backup Disk/Backups.backupdb
Sep 7 16:26:00 Bento-iMac KernelEventAgent[47]: tid 00000000 type 'hfs', mounted on '/Volumes/My Backup Disk', from '/dev/disk1s3', low disk, very low disk
Sep 7 16:26:00 Bento-iMac mds[45]: (Warning) Volume: Indexing reset and suspended on backup volume "/Volumes/My Backup Disk" because it is low on disk space.
Sep 7 16:26:02 Bento-iMac mds[45]: (Normal) DiskStore: Reindexing /Volumes/My Backup Disk/.Spotlight-V100/Store-V1/Stores/35367D91-8096-4D43-802B-A8658DBAB581 because no basetime was found.
Sep 7 16:26:02 Bento-iMac mds[45]: (Normal) DiskStore: Rebuilding index for /Volumes/My Backup Disk/Backups.backupdb
Sep 7 16:26:04 Bento-iMac mds[45]: (Normal) DiskStore: Creating index for /Volumes/My Backup Disk/Backups.backupdb
Sep 7 16:26:14 Bento-iMac com.apple.backupd[56515]: Error: Flushing index to disk returned an error: 0
Sep 7 16:26:14 Bento-iMac com.apple.backupd[56515]: Copied 776 files (17.3 MB) from volume iMac HD.
Sep 7 16:26:15 Bento-iMac com.apple.backupd[56515]: Backup canceled.
Note the "error: 0". Error code zero normally indicates success.
There were also many, many, many copies of the following message, which occurred while Spotlight was trying to index the backup disk:
Sep 7 17:28:40 Bento-iMac com.apple.backupd[58064]: Waiting for index to be ready (100)
Here's what I think is happening: at the very end of the backup, after the files have been copied to the backup disk, mds resets indexing because the disk is now full. backupd's attempt to flush the index to disk then fails because indexing is suspended (error zero), so the backup is canceled. I suspect that this may occur when the new backup and the old one(s) being deleted are both small enough that the disk "packs" tightly, leaving no room for the index. If a large (>500MB) old backup had been deleted to make room for a small (<100MB) new one, the problem would not have occurred.
I worked around the problem by switching Time Machine from the full disk to my Time Capsule. (I did not have this system backing up to the Time Capsule originally because I purchased the Time Capsule later for a different system.) The downside of this is that I lost access to older backups (though they are still accessible by right-clicking on Time Machine in the dock and selecting "Browse other Time Machine disks..."—however, I have not actually tried this). I'm also not completely happy having both my main systems backing up to the same hardware, but everything seems to be working well at this point and I do have a secondary backup system, using SuperDuper to clone the systems' disks to an external HD, which I do about once a month.
Although I have worked around the problem, I am posting this in the hope that it will be useful to someone else, in the hope that someone at Apple will notice and perhaps improve the performance of Time Machine in this situation, and also in the hope that someone can suggest a solution that does not involve throwing a bigger disk at the problem. Is there any way to free up space on Time Machine's backup disk, for example by manually pruning older backups, either through Time Machine itself or via the Finder or command line?

If you suspect that the disk being full is the problem, have you tried deleting some of the old backup data on the TM disk?
When in TM, go back to the past a long way, right click on a file/directory and select "delete backup". Do this on some big files you have (so that you get more space per removal) that you change all the time (so you'll still have recent backups).

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The post got this reply:
Thx for your #2 tip on using Time Machine with an Airport Extreme Base Station, then switching to a wired connection. Worked perfectly.
Started the TimeMachine b/up wirelessly, allowed it to run for a couple minutes, then stopped it, unplugged the USB drive from the AEBS, plugged it into the computer directly via FW400, opened TimeMachine and it recognized the Disk. Ran TimeMachine via the wired connection, after it finished I ejected it, plugged it back into the AEBS, initiated the AirDisk in the finder, then opened TimeMachine and presto!!
Awesome tip. Note: this works for first-time TimeMachine wireless backups only. Saved me over 40 hours of wireless waiting!!
http://gizmodo.com/370017/how+to-use-time-machine-with-an-airport-extreme
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Time Machine does not backup all files

I recently did a clean install and to my horror i can see that Time Machine does NOT back up all my files.
It seems to be worst in my music library which fortunately is pretty easy to rebuild do to itunes index.
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Or is it just broken and should be avoided?
I have 1,5 year old Macbook Pro Retina 15 inches 500 GB SSD

If you use the third-party application "Dropbox," you may see files in the Finder that are not present locally, but are actually on a network server. Those files won't be backed up and won't appear in Time Machine, even though they show in a Finder window. If the files in question are in a Dropbox folder, disable the software or refer to its developer for support.
Continue only if you've ruled out Dropbox or any similar product as a possible cause of the issue.
Open the Time Machine preference pane and unlock the settings, if necessary. Click the Options button. If there is one particular folder with items that are not being backed up reliably, add it to the list of excluded items. If there are many such folders, add your home folder to the list, or add a whole volume (i.e., what Apple calls a "disk.") Save the changes.
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Time Machine does not backup all of my files

Hi,
If I compare my Dropbox folder to what Time Machine backups there are differences which means that Time Machine does not backup all files:
diff <(cd "/Users/phil/Dropbox" && ls -R | sort) <(cd "/Volumes/TimeMachineBackup/Backups.backupdb/Computername/Latest/Macintosh HD/Users/phil/Dropbox" && ls -R | sort)
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I did not exclude the folders affected from the Time Machine backup.
I have verified this behaviour on other computers as well.
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Philipp

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2) Open your Terminal app (Located at /Applications/Utilities/Terminal)
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Make sure that there are no other Macs backing up at the present time.
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Count to ten
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