Considering the entire purpose of the forum is to post DIY tutorials and step-by-step guides, I'd rather contribute than pay to host my stuff elsewhere.
What's the forum?
Without seeing it, it seems to me the guidelines on post length are there for a reason. If the guideline on length is a restriction on the posting of reasonable tutorials and step-by-step guides, though, then that seems like a reason to increase the allowable length. For everyone, not just for you.
If you guys have no help, then thanks anyway.
Think about what you asked for.
You asked for someone to write a script, or provide step-by-step instructions for you, to perform a task specific for you. This forum isn't a "write me a program" forum. It isn't really a step-by-step instructional forum, either, though that might occur if the steps are brief.
You also said you thought it might be fun to automate it. So where's the fun if someone else does all the work? Watching it run? Fun for you maybe, not so much for whoever wrote it.
Maybe you should break it into two problems: splitting to meet word-count requirements, and posting data. You can do the first and write it to files. Or simply insert markers like "-----" at the right places. Then you can at least copy/paste properly sized posts manually. Then do the auto-uploading later, perhaps by breaking that task down into smaller pieces. Oh, and write the whole thing up as a how-to article.