I use the 2520 with 2509n reel all the time, being my first and only method so far. I'm relatively new to LF and absolutely new to film development in general.
I also load the reel in a cheap changing bag, so you might have an advantage if you use a tent or a proper darkroom.
Nonetheless I don't really have any problems loading up the reel, it's a matter of practice and by the second try you shouldn't be struggling, really.
I tend to use my left thumb to spot the guidelines on the top, starting for the inner, and my right hand to handle the film and push it inside.
I'm really not sure whether the 2520 can be used with the CPE-3 processor or not.
I also had considered the drum expert but it was way too pricey. To be honest, Jobo products seem to be way to expensive for what they are, basically plastic cilinders and reels. But they get the job done so yeah...
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