Can't say much other than 'yes it is not posting to WU' without seeing more 
of the log ie from weeWX startup. You can use wunderfixer 
<http://weewx.com/docs/utilities.htm#wunderfixer_utility> to re-post to WU. 
In fact it is a good idea to set up wunderfixer to run by cron on a daily 
basis, I run it at 23:58 each night. WU is by no means perfect and despite 
seeing 288 posts to WU each day in my logs some just don't make it.

As to your previous questions. Twitter should not be that hard to set to 
work, I would be getting everything else back and stable before worrying 
about twitter. The error in the log indicates that python cannot find the 
requests_oauthlib module. This is not included in the standard python 
install, did you ever install it separately? Re-installing it would be a 
good starting point. You may also find more info by searching the forums 
for 'twitter' or maybe by looking at any comments at the start of the 
bin/user/twitter.py 
file.

I think Tom covered the downloading of data from the logger, another easy 
way to tell if the last 27 hours of data has been downloaded OK is to look 
at your daily plots. They default to 27 hours of data with no aggregation 
and any (extended) missing data will show up as one or more gaps. Week, 
month and year plots use aggregated data so gaps may not be apparent there.

Gary

On Wednesday, 24 May 2017 11:22:12 UTC+10, Peter Dougherty wrote:
>
> It's doesn't appear to be sending any of the missing data to Weather 
> Underground, but it *is* sending current data. The station went back 
> online around 18:29 today (23 May) and had been offline starting around 
> 05:00 on 17 May. Three hours after going back online I cannot find the 
> missing data on the WU site.
>
> This is a log excerpt. It appears as if it's trying to send the backlog 
> (there are hundreds of these entries in the log).
>
> .
> May 23 18:34:32 wx weewx[1905]: manager: added record 2017-05-22 02:20:00 
> EDT (1495434000) to database 'weewx.sdb'
> May 23 18:34:32 wx weewx[1905]: manager: added record 2017-05-22 02:20:00 
> EDT (1495434000) to daily summary in 'weewx.sdb'
> May 23 18:34:32 wx weewx[1905]: restx: PWSWeather: Published record 
> 2017-05-22 02:15:00 EDT (1495433700)
> May 23 18:34:33 wx weewx[1905]: restx: CWOP: record 2017-05-22 02:20:00 
> EDT (1495434000) is stale (144873 > 60).
> May 23 18:34:33 wx weewx[1905]: manager: added record 2017-05-22 02:25:00 
> EDT (1495434300) to database 'weewx.sdb'
> May 23 18:34:33 wx weewx[1905]: manager: added record 2017-05-22 02:25:00 
> EDT (1495434300) to daily summary in 'weewx.sdb'
> May 23 18:34:33 wx weewx[1905]: restx: PWSWeather: Published record 
> 2017-05-22 02:20:00 EDT (1495434000)
> May 23 18:34:33 wx weewx[1905]: restx: CWOP: record 2017-05-22 02:25:00 
> EDT (1495434300) is stale (144573 > 60).
> May 23 18:34:33 wx weewx[1905]: manager: added record 2017-05-22 02:30:00 
> EDT (1495434600) to database 'weewx.sdb'
> May 23 18:34:33 wx weewx[1905]: manager: added record 2017-05-22 02:30:00 
> EDT (1495434600) to daily summary in 'weewx.sdb'
> May 23 18:34:33 wx weewx[1905]: restx: PWSWeather: Published record 
> 2017-05-22 02:25:00 EDT (1495434300)
> May 23 18:34:33 wx weewx[1905]: restx: CWOP: record 2017-05-22 02:30:00 
> EDT (1495434600) is stale (144273 > 60).
> May 23 18:34:33 wx weewx[1905]: manager: added record 2017-05-22 02:35:00 
> EDT (1495434900) to database 'weewx.sdb'
> May 23 18:34:33 wx weewx[1905]: restx: PWSWeather: Published record 
> 2017-05-22 02:30:00 EDT (1495434600)
>

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