That helps,
A lot of people get into this business looking at the auto/truck graphics as a step into it, Banners is a natural since they are simple, not a bad start, but there is a lot of competition, especially in your location, be prepared for it.
One way is subscribing to magazines like Signcraft, and books on truck graphic layouts and books like "Mastering Layout" by Mike Stevens or Dan Antonellis' Logos for Small Business( I think thats the title) Great resources you have on hand.
Next is if you have experience, you should some knowledge of a vector software, (Corel, Illusrator, Freehand or Canvas) Maybe you should stick to the one you are used to, and use a bridge program to start-Cocut comes to mind.
As far as a cutter printer, Roland may sound good, but look into it carefully, the money it takes to operate makes it an expensive chouce in the long run, to be honest the Edge in NOT the high end option, in fact it's more the entry level solution-when copmpared to an Arizona, Gerber Maxx, 3M Scotchprint.
With no expereince in the business, and none is color software like Photoshop, you already have a lot to learn, I would suggest finding a vendor, the area you are in must have a lot of choices, look into them before you make a choice. On the point of design experience, you were not totally clear how much, try going to
www.creativehotlist.com or check out the work here, see how you compare to the better designs, it's alwys a learning experience, but you can learn a lot by the great work posted on this and other boards.
I say start posting in the portfolio section and get a feel at where you stand, if you do have a software preference, great, if not-pick one, and start immediatley in training yourself, the more practice the less it gets to putting your design into reality. Most of all have fun with it, it is a great way to release your creative side, as long as you know that design is worth something, and other sign guys have to many low ballers to compete with, try to start getting paid as quickly as possible.
On equipment and software, I have used almost every brand out there at various sign shops-the better ones I have used are Summa, Graphtecs and Gerbers.
Software, I use Illustrator to design in, I started in Corel, and it's a solid program, but since I design for print as well as for sending out to other shops, Illustrator is the most "neutral" software. Good luck on your decision and don't be afraid to ask any questions, there is a great group here.