I have a short story that I am tired of trying to sell but just can't let go of. It's been through a number of revisions so the writing is pretty tight. I've been wanting to turn it into a comic for a long time.
My questions are:
1) Should I just jump in and start drawing it, or should I rewrite it as a script first?
2) Should I upload it as I go along, or upload the whole thing once it's complete?

Upload as you go. That's the best way to build an audience

1) Different people have different creative processes that work for them. Generally speaking, you should have your pages storyboarded out in advance, rather than just hoping you'll get the perfect layout your first go 'round. Of course, that's "ideally speaking!" I don't do that, personally.
 
2) 100 percent agree with MrHades. The worst possible thing you can do is post it all at once then just let it disappear into obscurity. You should start out maybe posting a page a day, then settle into some kind of regular or semi-regular update schedule, and try to keep a page buffer if at all possible. Again, that's "ideally," though!

Thanks, El Cid and MrHades.
I have to ask, El Cid, if you don't storyboard, what DO you do?

jwideman [..] wrote:
I have a short story that I am tired of trying to sell but just can't let go of. It's been through a number of revisions so the writing is pretty tight. I've been wanting to turn it into a comic for a long time.
My questions are:
1) Should I just jump in and start drawing it, or should I rewrite it as a script first?
2) Should I upload it as I go along, or upload the whole thing once it's complete?

Given that you've spent a great deal of time getting your writing tight, you would probably be more satisfied with the comic result if you convert your story to a script before you begin drawing. There are many differences between the story and comic medium which may not occur to you until you start deciding to do the actual layout. Like, a regular mistake I made when I first started adapting my own short stories into comics was now allowing enough space for the text. In a story, if a character is talking, you can just wrap his dialog to a new page. But in a comic, you have to have interesting visuals along with the text. You can only fit so many panels and so many words in each page. 
And by "script," I'm not necessarily saying a formal script. 
What I do (not that I'm always right, but it may be useful to hear how others do it in order to develop your own work flow) is, once I have written my story in prose, I copy and paste text into the Comic Life Magiq program I use for layout. This lets me see how much space the words take up in the comic context. I draw panels on each page, put the speech bubbles and text boxes roughly where I think they will go, and add a short line to tell me what I think I'll be drawing in the panel. I do this scene by scene. That is, I don't draw anything for a scene until I have a rough idea of the composition of the pages associated with that scene. Drawing always seems to take up the most time, so I want to make sure I don't do more work here than I have to. Like, I'm working on this super hero book right now. I wanted to have two characters talking in a car. Realized that, what read as a few pithy pages of dialog in my short story version, turned into eight pages of comic panels. Decided that this should really be 2-3 pages, so cut down the dialog (and thus, dramatically reduced the number of pictures I had to draw). 

I use thumbnails to plan out pages once the script is complete. Like this:

http://www.drunkduck.com/Vanguard/5353270/

Thansk, Allyndn. I have Comic Life, so I expect I'd be able to format the dialogue the same way. What did you do for your non-dialogue narrative?

jwideman wrote:
...I have to ask, El Cid, if you don't storyboard, what DO you do?

 
Now that I think about it, I guess that what I do is like mental storyboarding. I usually start by making all my panels, just mentally knowing what's going to go in them, and then I plunk in the artwork.
 
Allyndn made some very good points, especially about dialogue. I also do a lot of work with the Lite Bites Review comic and it's amazing just how cumbersome a wordy review becomes when you convert it into speech balloons. I'm not very good at this personally, but ideally in a comic you should keep all the dialogue (and text in general) to a necessary minimum. Too much text can be intimidating, and not visually attractive.

Sounds good so far, guys. I've scripted the first two pages (of the script - still on the first page of the story). Should I script the whole thing or do a page with each update? I'm eager to get started, but is there something I might be overlooking?

You should just do a couple of pages at first, to get your workflow down, then you should be able to start rockin' and rollin'.

I've taken the plunge and got the ball rolling. I'm going to have a few weeks of extra free time, so I just might get the whole thing posted in a month of daily updates.

jwideman [..] wrote:
I have a short story that I am tired of trying to sell but just can't let go of. It's been through a number of revisions so the writing is pretty tight. I've been wanting to turn it into a comic for a long time.
My questions are:
1) Should I just jump in and start drawing it, or should I rewrite it as a script first?
2) Should I upload it as I go along, or upload the whole thing once it's complete?

1. Writing a script for a comic based on a short story while similar in principle isn't quite the same; you have a slightly different beat to march to.
When I decided to start my comic Child Snatcher, which was also based on a short story that I had writen, I found converting it to a script presented its own unique challenges. Because the intention was to release it for the web, I had to consider an entirely different pacing. For example, I had to make sure that my high/suspense points hit the final panel of the page.
If you're planning a physcial print distribution, then you have to worry a lot less about when you hit the cliff-hanger as it will land on the last page of the issue (in theory encouraging the reader to buy the next issue). 
I wrote the script first. I planned the arc and wrote it out start to finish. However, I just made sure that I was rather loose with the description and number of pannels as I knew I would be the one drawing it. I just made sure that all the relevant content for that particular beat was present and I could sort out layout when I reached that phase.
2. I would create a schedule to upload to. 3 times a week works great and helps to build momentum as each piece is published. Say you have a 24 page issue. Unless you have some mad marketing skills you might not see the results that you want in the first little while. Publishing a page a time will give you time to market and purchase ad space to promote your work. The anticipation of reading the next page is part of the draw to a comic, so use it to your advantage. 
Personally I would draw it all before uploading because that gives me a nice buffer while I work on the next issue. This way readers won't be left hanging and you can adapt your site/style well in advance.

As my comic is based on a short story I wrote, I thought I'd chime in with my two cents for what they're worth.
I'd say start drawing it, then release pages gradually. (agree with the others).
I'd also say, do the revisions as you go. Comics are a different medium than the written word. In the written word you use the reader's imagination to "fill in the blanks" of the world. In comics you have to fill in the blanks. Also I've found some of the original scenes and dialog just didn't work in comic format. It sounds like you've already refined the story, but, I'd warn you may still have to revise it for the comic format.

One thing I found with my comic was that the story that worked in text was too thin for visual medium (you'd think it would work the other way around), so I had to rewrite parts of it and add characters and a few scenes. (there were only two primary characters in the original) So, my advice is to jump in and revise as you go.