Tips for getting started with my first messenger bag

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I just picked up Lisa Sorrell's book on leather inlay and overlay, and now I have a burning need to make some bags as a place to showcase the applique I'm going to make of my favorite dumb video game characters.

From what I've seen and read, basic messenger bags are basically a couple rectangles with a gusset to bridge between them, which seems like something I shouldn't have trouble making a pattern of; I also have the Stohlman books on leather cases, which have a lot of nice tips for handle attachments etc. even if they're geared toward hand-sewing and veg tan.

There are just a couple questions that are keeping me back from getting started:

  • I really, really don't want to hand-sew.  I do have a Consew 227 (cylinder bed walking foot) set up for leather, so I should be able to handle most reasonable bag leathers.  Keeping that in mind, how does one actually stitch down the gussets?  Are there any tricks I should know about?
  • In order to sew down the applique with a roller foot, the bag (or at least the portion I'm sewing the applique to) needs to be of a light enough leather that I can sew it on the roller foot machine (I have a direct-drive, needle feed flatbed garment machine that I plan to put a roller foot on).  That limits my leather choices - I don't think making the whole thing out of veg tan is going to work for me.  What are my options for stiffeners?
  • Relatedly, what's a reasonable leather choice for a semi-soft messenger bag? I have some leftover bullhide from the Hide House I'd like to use up, but it might be too spongy to work well.

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