My friend, Mercedes Yardley, author and slush reader at Shock Totem Magazine replied in an email about this:
Quote:
Hi Tim!
I'd always suggest submitting to markets over self-publishing for a few different reasons.  The market is always changing, of course, and self-publishing is rapidly losing the stigma that it once had, but there is still a stigma.  While some self-publishers go through the same editing and vetting process that a paying market goes through, there are still quite a few examples of people that write it on Friday and offer it on Amazon by Saturday, for example. The pieces aren't critiqued and edited like they would be if they were going through a tradition market.  In a sense, this tends to leave a stain on the self-pub label.
I'd also suggest going through a paying market because 1) you'll get HWA and (if you choose from the list of qualifying markets) SFWA credit.  I'm a member of both these organizations and I enjoy them.  I do better as a writer if I have a certain goal that I'm working toward.  "Qualifying for the HWA" made me strive for pro-paying markets when I might have been tempted to give the pieces away.  There are also perks.  For example, there are a few HWA only anthologies.  If you're not a member, you can't submit to them.  Also, I was lucky enough to interview a few of the SFWA Nebula nominees for the SFWA site last year.  I couldn't do that unless I was a member.  And once you're an active member, you're able to compete for awards.  That's extremely motivating!
Besides that, if you submit to traditional markets, you'll make relationships that you most likely wouldn't make otherwise.  These relationships will enrich both your personal life and your career.  If I hadn't submitted to Shock Totem, then I never would have met the crew.  They never would have embraced me, and I wouldn't be working with them now.
Ultimately it's your choice, of course, but this is what I see. Also, another idea is to keep your short stories and make a collection out of them, which is what I'm doing. I wish I had a few more unpublished stories to go into it.  Everything you write, no matter how displeased you are with it at the time, is gold, so keep them filed away somewhere.
And Aubrey, I'm still looking for that $5 cover website. I can't remember what it was called, but a writing podcast mentioned it as a good idea for short story covers.