Silhouette Cameo : new experience

So today I've tried the print and cut feature from the Silhouette. I meant to create brand new tags for my products as the current tags are a bit rustic to say the least.

I chose a tag design and added the information. Then I multiplied the design to fill the page and it all looked pretty easy and perfect.

For the printer I have an HP Officejet G55, kind of an old printer, but really sturdy and it's been running perfectly for over 10 years now. I usually have it connected to my old computer, which I only turned on for that reason alone and it was getting frustrating. Now, with the Silhouette I finally had to make a decision so fortunately I was able to find a cable that did the trick and the printer was ready to go!

I quickly hit my first glitch as the printer doesn't print any text I add with the Silhouette Software, which means that the only way I had to add text was to create a jpeg file with the text and then add it as an image. I had no idea it worked like that.

With that problem solved I printed the first one and went to the silhouette for the cut part. Let me tell you, getting the machine to recognize the markings is sooo troublesome! I've googled and there are actually some people who haven't been able to do it AT ALL! I manage to do it, after a couple of tries, from what I gather, you can't really push the mat to the rollers, you have to keep it out and let the machine pick it up or it will skip the registration marks.

With that done, the cutting did not match the design on the screen. The first two were perfect, and then it starts to drag more and more and by the last one it's completely off the mark. I wanted to scream!! I tried and tried, I calibrated the machine, it is now perfectly calibrated according to the test but it still drags!
I guess I'll have to adapt the images I see on screen to match the end result, but I'm pretty sure I shouldn't have to, so I am beyond frustrated!
I've tried everything I could think of, but since the first column works, the 2nd starts to shift and the 3rd and 4th are completely off the mark, I really don't understand.
Initially the flowers (it was a flower tag) looked kind of oval, so I thought it might have to do with some fit to page feature I was selecting wrongly, but I can't really see where I can change that.

So by now I've ran out of ideas and I feel like I need to leave it aside for a while and maybe start all over again later... :(