I-web crashing during upload to server

I am using iweb 08 on an intel imac with OSX 10.4.11
I can't seem to upload to my web server (network solutions) without crashing somewhere in the cycle.
The website is photo intensive. The images are fairly large but have been optimized to about 70% of original.
I use RAGE webcrusher software to optimize the file.
The final file size is approximately 29 MB,
I am uploaded with comcast cable.
Is this file too big for iweb?
What would cause this to keep getting hung up?

Thank you Wyodor for your questions so far.
I guess I got my story out of sequence.
The path I follow is to:
1) Publish i-web to a folder
2) Bring the i-web folder into Webcrusher to optimize
3) Drag the site files and index files into FTP software (Panic-Transmit)
4) Commence upload to web server
The compressed file size that is being uploaded is about 29 MB.
It usually takes about 40 minutes to complete the upload.
Sometimes the whole process works and my website is uploaded.
Sometimes it gets hung up in the transfer and goes IDLE.
The hang up happens erratically. Sometimes it stalls 2 minutes in and sometimes after 20 minutes.
I have repeated this on two different mac computers at home: Intel i-mac OSX 10.4.1 and MacBookPro OSX 10.5.8.
I have uploaded the Webcrusher files to Drop Box and am now going to try this on a newer i-mac at myshop.
The new one is running OSX 10.6.8.
I don't have any FTP software for the new machine but will search around for that soon.
Could this have to do with the overall size of my i-web file or is it just out of date boxes and inappropriate FTP software?
For what it is worth: The only changes I made to the file since last it updated easily updated was to add a lot of text to an already existing page.

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