Well you'll make it easier on the CAA going over your case history with regards to tasks completed and aircraft and so on, but when i applied for my licence a while back some of the jobs listed were not listed in date order, i did speak to a surveyor who advised me it is good practice to keep everything in order as it is easier to follow an individuals progress, but that said, it's not the end of the world if you have'nt listed it all in date order, but i would send in a CV with the log book just to give them a quick appraisal of what you have been doing.
When it comes too a type rating everything should ideally be listed chronologically and in ATA Format, is it avoids being rejected at the first stage,this was learnt from experience.
Good luck