i currently use a ipad pro 11 with a mac mini , the pro i use all the time on the road with no issues , i got the logitech slim folio with it. works great.
i would definitley get applecare , i have never used it yet but since its moving with me all the time its a risk worth the 100$ for me.
i use the ipad pro to manage VM's at home , VPN , managing cloud services , SSH sessions. never had an issue.