You mentioned this is to put a photo on a shirt. What kind of white does the photo have that you are cutting out?
Usually photos are already rectangular. If you have alot of background, would you crop that out? Or add a background so you don't have to trim the image at all for this order? You're a photographer, so I'm guessing you use Photoshop.
If you don't want to outsource
DTG (this is a very nice end product, and you yourself are putting forth no effort and time), and you want to go heat transfer paper,
JPSS is the best paper IMO for the job, if you can manipulate the photo to eliminate the need for trimming, then you only need the
JPSS and your printer. Did you mention you have to C88, or you are looking at it?
Either one of these methods takes the cutter out of the equation, reducing your immediate $$ outlay, and learning curve.
Re: Photographer needs advice on Plotter? 
