HI Troy
I did something very similar awhile ago and didn't have any issues.
As Vince said "use a new sd card to build the new system"
What made my transition easy was the weather console has a memory that
holds approx several days of data.
If I stop weewx for some reason and for some hours, then restart it, weewx
appears to retrieve the missing time interval.
This helped by keeping the original database intact.
The new sd build database would be discarded when the new sd card was
finished.
So over a few days I just swapped between old and new until I was happy
with the new setup.
Then just copied over the files I wanted .......just mounted the old sd
card on another pi and copied the files over.

regards ian p

On Tue, 10 Nov 2020 at 02:14, [email protected] <[email protected]>
wrote:

> Hello,
> When I initially setup weewx, I was very new to raspberry pi OS and so I
> used what I had currently had on hand, a RPi I got a couple years ago which
> was running Jessie. Recently, I've realized there are some issues, mainly
> Python2.7 and Python3.8, that basically boiled down to running Jessie vice
> the new Buster. If anyone is wondering, the SSL module was having issues
> installing updates via pip command and it came down to the OS.
>
> Anyway, I plan to create a new SD card with Debian 10 (Buster) and then
> install weewx. I've read upgrading OS from Jessie to Stretch to Buster
> could take quite a bit of time and there is a risk to losing data. My
> question comes, what's the quickest way to get weewx running, as it is
> configured now, on the new OS? Ensure I backup my weewx.conf, weewx.sdb,
> and skins? Is there anything else I should be conscience of when moving? Is
> there an "easier" way to do this? Just worried I'll be down for a while
> trying to configure and get everything up and running as it is now.
>
> Thanks,
> Troy
>
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