For me, the difficult period lasted for the first six months. Everyone heals differently though, it's important not to judge your own recovery based on how long it takes others. Your body is unique and will recover at it's own speed.
As for the length of time it takes to get to depth, that used to be a big problem for me. There were times when it took over an hour, and that can be very upsetting and frustrating. Just remember that if dilation gets difficult or takes longer, it's a sign that you need to make your dilations last a little longer or even do an extra one every now and then. If things get tough, don't let that keep you from doing your full dilations for the full amount of time (and always start keeping time AFTER you are at full depth).
It can be so stressful in those first few months, but I promise that it gets easier. Just keep up with your routine!
*hugs!*