We just did the Chase biz checking deal a little over a week ago (spouse and I each did one at separate times). I know what you mean about getting out of your comfort zone!
It was painless for both of us, and spouse is fairly reluctant to do this stuff--even that went smoothly. I did end up sharing more about my business that on a credit card app, so be prepared to answer basic questions about how much you'll make and spend, how frequently you'll use the account, and a little more detail about what you do (as opposed to just selecting a category on a dropdown). And the banker who helped me chatted about my business quite a bit. If it was a "business" that might've been a little more unsettling for me, but still nothing to worry about if you've thought through before you sit down. And my banker wasn't making any real judgements or decisions about the account, he was just filling in the forms on his computer.
It was only $300 when I did it, but just got an SM back that they're going to change me over to the $500 since I sent them a new promo code.