In regards to him having trouble scanning checks with Chase: that sounds like a problem with Chase's implementation, not the technology as a whole.
I have been using USAA's online service as my only form of check deposit for 5 years (started with flatbed scanner, now iphone). I have never had a check refused. Hundreds of them have gone through (have to re-take the photos sometimes, but they always eventually work). It works, and it works really well.
In regards to him having trouble scanning checks with Chase: that sounds like a problem with Chase's implementation, not the technology as a whole.
I have been using USAA's online service as my only form of check deposit for 5 years (started with flatbed scanner, now iphone). I have never had a check refused. Hundreds of them have gone through (have to re-take the photos sometimes, but they always eventually work). It works, and it works really well.