one actual advantage of htc dev is that the only way you could not easily re-root is if they released and OTA that relocked your botloader,and removed unlock support
i do not think that will happen.
however,if you have a custom recovery in place,you cannot accept the OTAs. the custom recovery is unable to install firmware and other aspects like the stock recovery does,and attempting to jam you up to a point where recovery is difficult(potentially impossible)
cases OTAs can be accepted naturally while rooted,by leaving the stock recovery in place,however,alot of factors must be correct,so simply leaving recovery stock does not gaurantee OTAs will succeed.
your best bet if you want to be rooted,as has been mentioned,is DO NOT ACCEPT OTAs. rom devs will bake the updates into custom roms you can flash in recovery,and the firmware packages will be pulled from the OTA downloads for you to manually install on your phone.
so dont worry,your not stuck without updates. youll just have to apply them more manually,rather than trying to accept an OTA on the phone.
hope that all made sense