The Self-Pub Adventure

I am about to dive in where others have gone before. I’ve finished revising my last backlist title. It took me quite a while, as the doc file is over 500 pages and I made lots of changes. Now comes the next stage, which is to hire a cover designer.
Wait, not so fast. First, I need to determine the back cover copy. That’s not so hard. I can use the same one that’s on the original paperback with a few heading changes. But inside the book are more challenges. There are several introductory pages containing an excerpt, review quotes, and a dedication. I ditched the latter, as those people no longer apply to my current career. The excerpt and quote are reusable with some slight modifications. But what now? Do I add them to the front of my doc file? Should I include a title page? Maybe on Smashwords, these things are delineated, but I haven’t gone there yet to read the requirements. First I have to get a cover.
Getting a cover will probably necessitate filling out a description of the hero/heroine and a suggested background scene. I already have a list of cover artists garnered from other authors’ online posts. But now I must prepare these materials for when I contact one of them. Hopefully the artist will determine the proper fonts and where to put my name and book title. And I have to remember to state somewhere that this book was previously published and written under a pseudonym.
This whole process seems daunting, but I’d like to use this book as an experiment. Because who knows, if my current works on the market fail to sell, I may choose to go this route. Or I may just get tired of waiting for a response and then waiting another year or two for the book to be published.

It’s a scary thought for an author who has only sought traditional publishers or legit e-book pubs before. Plus, self-published works are still not accepted by many reviewers or booksellers for signing events, so there is a certain loss of prestige.
I know some of you have already cast off the shackles of print publishers and ventured into this new territory. Are you happy with your choice? How many of you have done it for original works?