I would personally recommend using the pi3b+ to set up a clean new v5 setup 
rather than worrying upgrade scenarios....

   - install the latest raspios 32bit on the 3b+
   - install the latest weewx v5
   - configure it to run the Simulator (initially) to get it running and 
   stable running a simulated station
   - install any extensions and skins you've added.  Probably set 
   enable=false for anything that uploads to other systems (initially)
   - maybe set up the RTC and get that working on the 3b+ if you have one 
   to install there too
   - in short - get a full setup working vs. the Simulator  and vs. a 
   webserver (I use nginx) of your choosing

If you're running the Vantage driver getting the 3b+ to work with v5 is 
straightforward and you can keep using the zeroW attached to the Vue until 
you get the new pi set up to your liking using the Simulator.

Re: the db schema, you'll need to check your db for whether you're using 
the old smaller wview schema or the newer wview_extended schema.  If you 
need to convert it to the new schema do that offline on the 3b+.  Not too 
hard to do but it might take a while depending on how many years of data 
you have in your current db.  Instructions are 
at 
https://www.weewx.com/docs/5.0/utilities/weectl-database/#reconfigure-a-database

Once you're running the bigger schema in your zeroW actual db, you would 
stop weewx on the 3b+, move the archive/weewx.sdb file and public_html tree 
aside,  copy your actual db into the archive directory, switch to the 
vantage driver, and start weewx up.   Assuming you have a Davis logger 
weewx will backfill any needed records the logger captured from the Vue. 
You can't really hurt anything if you mess the procedure up a time or two, 
but it's pretty straightforward.  You'll have the zeroW db there just in 
case.

You can check to see if you're already running the extended schema in your 
db already by just counting the number of fields:
         echo "SELECT count() FROM PRAGMA_TABLE_INFO('archive');" | sqlite3 
weewx.sdb

The extended schema will return a count of 114.   The original schema had 
around 53 or so if I recall correctly.  If you're weewx 3.x you are 
probably going to see 53 as your answer.

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