You configure from scratch every time? My LAN Debian server installation is 10 years old and has had two in-place upgrades. I have changed the motherboard, migrated to RAID-1 for /home and an SSD for / during that time. Config file changes are flagged by the installer (the same as happens during updates, if the .conf changes) and you have the opportunity to stick with the old, change to the new or edit as you go.
I have approached each upgrade with trepidation and allowed a full weekend, but it has always (so far ...) been back in use in under two hours, start to finish. That's including a full image of the root drive (/home was imaged the day before – it's 2 GB). One of those upgrades included a change from sysv to systemd and from i386 to amd64. I did a test run in a VM before starting that one for real.