Like most others here, I don't generally mind box pressed cigars, but do prefer the feel of rounds. The "harder" the press, the less comfortable the stick is for me, and it also tends to make it more difficult to manage the burn by rotating the cigar as I smoke it. I don't recall having smoked any pressed cigars over 50 or maybe 52 ring, as I don't like the feel of cigars any bigger than that anyway, but I can see how anything larger could be troubling.
A box press doesn't stop me from buying a cigar I like, and there are some that I buy many of (Padrons, VSGs). However, if the same cigar was available round I would likely buy it rather than the pressed.
One way of "depressing" these cigars may be to overhumidfy them for a short time. The VSGs at my B&M are in the wettest part of the humi and have to be dried out when I get them home (I just bought one the other day, and it literally fogged up the inside of the baggie), but they are much less square than when they arrived from the factory.