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... and here's what that will look like cut in one color.

Is this what you're after? The trace is really ruff, but i did it all in Inkscape in about a minute.

I suggest Inkscape. It's a great free editor. Working with vectors does take a while to wrap your head around but once you get the hang of it I think Inkscape is pretty intuitive. The other big design programs are Adobe Illustrator, and Coral Draw. Both are extremely powerful but also rather pricey. You can also upgrade VM, a bit cheaper and it is a pretty good design program as well although it does things different enough from Inkscape that I still struggle at times trying to do what I think should be really simple. Not that VM can't do it, it just does it in a different way from what I'm use to.

Start with Inkscape. It's free. Once you get your feet under you you can make more educated choices. Vinyl Master has several levels of ability and the Cut Level version is mostly a cutter interface to communicate with the cutter, the next step up Letter Level is more advanced and has more sign builders tools. There is a comparison chart on their website. If you stay with them (great choice if you are a windows computer user) I would suggest the Pro Level if you don't expect to need the printing options in the Expert Level. I am a mac user and have experience with Adobe so I stick with that but it's expensive and a major learning curve to figure it out. I use a different cutter utility that is mac compatible to actually cut. Mac's are great for graphics but they are picky what they will run and I don't get into the parallels or loading a windows OS into mine. For me the point was to evade the windows instability.

Your welcome, We do try here, but sometimes we can't get everything accomplished, when it is not made to be. Regardless, the Tripp-lite Keyspan adapter should help you with better communication on your SC.

You've done a whole lot to help me out so far though and regardless if this get's working the way I'd like or not, I want to thank you for how much you've been trying to help me out Thank you so much.

First, all graphics need to be in vector format for the cutter. Second, multiple colors is usually not an issue, as you should be able to select which color to send to the cutter (or you can select multiple colors to cut in a single job). Third, if there is overlapping in colors, and you're wanting them to be separate, if the logo is in color, then cut colors separately if the end product is a multi-color decal. If you're wanting the decal to be a single color, then be patient because this is where the fun begins ... you will need to choose a design/editing software of your choice, and start to get to familiar with it. This will not be your last logo that will come to you in multiple colors, nor will it be the first design you come across that will need some editing. So get to know a software that works for you - Illustrator, Inkscape, CorelDraw, Sign Blazer, Vinyl Master, etc.

It really depends on how long of a run you're going to do. Pre-feed, and check the drift. You can make an educated estimation for the starting point. Some software will start cutting from your point of origin, other software adds it's own margin of space. So the best answer to that is trial and error, but try really, really hard not to go off the vinyl and cut into the cutting strip.

There is no limit, put at least 1/4 inch away from the edge. We do not know how you have your cutter set up. Most don't own that cutter that reply back. Experience, trial and error. You will have to leave some room. I could with my cutter, but my cutter has great tracking (Graphtec) Use a pen tool and experiment.