Prob's with Batch Droplet File Renaming (ugh!)

I've created a few actions and turned them into droplets. I'm experiencing two problems with the way the droplet renames processed files that are going to cause some major headaches. I'm hoping there's a solution to these ;o)

1) Script asks if I want to save over a file. I may have two source files: file.tif
file.jpg

and I want to save them both as JPGs. It processes the first one, saves it as file.jpg, then goes to the second one, but then already sees a file called file.jpg and asks if I want to save over it. I can only save over, or cancel. I can't rename the file at that time. That's a problem.

2) It's TRUNCATING MY FILE NAMES! This is the bigger headache. I have it set to save them as Windows compatible file names, but it's truncating everything to 32 characters (like it's assuming it's Mac compatible). This causes two problems. a) I'll have to rename every single file reference in my database (HUGE PITA) and b) some long, but different file names are being truncated to the same shorter filename...which means I loose one of the two images.

Are there any fixes to this?

On issue 1:
1. Are you using File > Save for Web on this one?

2. Assuming you had two files in the \source folder named file.jpg
file.tif

What file names would you want each processed file to have?

On issue 2:
3. Looks like you're using File > Save for Web on this one, too. True?

1 = yes

2 = it really doesn't matter. It could be file.jpg and file-1.jpg for all I care...I just don't want one saving over the other.

3 = true. So, save-for-web truncates filenames? Is there any difference in JPG compression between SAVE AS and SAVE FOR WEB?

In the end, this might be moot. Since I ran into problems in photoshop, I decided to start writing the script I had held off on writing to resize images right on the server. Turns out .net has a fairly robust image resizing function that might do the job for us.