Este tipo de problemas es más complicado de asesorar, ya que puede venir originado en cualquier punto.
Lo primero es mirar el log como ya te han dicho.
Te muestro un trozo de mi log, aunque yo lo subo por FTP a un servidor local que tengo con un viejo Mele A2000
Nov 20 06:25:48 raspberrypi weewx[2073]: reportengine: ftp'd 37 files in 0.82 seconds
Nov 20 06:25:49 raspberrypi weewx[2073]: cheetahgenerator: Generated 2 files for report SteelSeries in 0.50 seconds
Nov 20 06:25:52 raspberrypi weewx[2073]: genimages: Generated 11 images for SteelSeries in 3.74 seconds
Nov 20 06:27:47 raspberrypi weewx[2073]: restx: PWSWeather: Failed to publish record 2016-11-20 06:25:00 UTC (1479623100): Failed upload after 3 tries
Nov 20 06:27:47 raspberrypi weewx[2073]: restx: WOW: Failed to publish record 2016-11-20 06:25:00 UTC (1479623100): Failed upload after 3 tries
Nov 20 06:27:47 raspberrypi weewx[2073]: restx: AWEKAS: Failed to publish record 2016-11-20 06:25:00 UTC (1479623100): Failed upload after 3 tries
Nov 20 06:30:17 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:30:18 UTC (1479623418) to database '/var/lib/weewx/cmon.sdb'
Nov 20 06:30:18 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:30:18 UTC (1479623418) to daily summary in '/var/lib/weewx/cmon.sdb'
Nov 20 06:30:31 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:30:00 UTC (1479623400) to database '/var/lib/weewx/weewx.sdb'
Nov 20 06:30:31 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:30:00 UTC (1479623400) to daily summary in '/var/lib/weewx/weewx.sdb'
Nov 20 06:30:46 raspberrypi weewx[2073]: cheetahgenerator: Generated 16 files for report StandardReport in 11.47 seconds
Nov 20 06:30:50 raspberrypi weewx[2073]: genimages: Generated 8 images for StandardReport in 3.40 seconds
Nov 20 06:30:50 raspberrypi weewx[2073]: reportengine: ftp'd 37 files in 0.71 seconds
Nov 20 06:30:51 raspberrypi weewx[2073]: cheetahgenerator: Generated 2 files for report SteelSeries in 0.52 seconds
Nov 20 06:30:55 raspberrypi weewx[2073]: genimages: Generated 11 images for SteelSeries in 3.70 seconds
Nov 20 06:32:50 raspberrypi weewx[2073]: restx: WOW: Failed to publish record 2016-11-20 06:30:00 UTC (1479623400): Failed upload after 3 tries
Nov 20 06:32:50 raspberrypi weewx[2073]: restx: PWSWeather: Failed to publish record 2016-11-20 06:30:00 UTC (1479623400): Failed upload after 3 tries
Nov 20 06:32:50 raspberrypi weewx[2073]: restx: AWEKAS: Failed to publish record 2016-11-20 06:30:00 UTC (1479623400): Failed upload after 3 tries
Nov 20 06:34:35 raspberrypi weewx[2073]: restx: CWOP: Failed to publish record 2016-11-20 06:30:00 UTC (1479623400): Tried 2 servers 3 times each
Nov 20 06:35:17 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:35:17 UTC (1479623717) to database '/var/lib/weewx/cmon.sdb'
Nov 20 06:35:17 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:35:17 UTC (1479623717) to daily summary in '/var/lib/weewx/cmon.sdb'
Nov 20 06:35:30 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:35:00 UTC (1479623700) to database '/var/lib/weewx/weewx.sdb'
Nov 20 06:35:30 raspberrypi weewx[2073]: manager: added record 2016-11-20 06:35:00 UTC (1479623700) to daily summary in '/var/lib/weewx/weewx.sdb'
Nov 20 06:35:45 raspberrypi weewx[2073]: cheetahgenerator: Generated 16 files for report StandardReport in 11.77 seconds
Nov 20 06:35:49 raspberrypi weewx[2073]: genimages: Generated 8 images for StandardReport in 3.39 seconds
Nov 20 06:35:49 raspberrypi weewx[2073]: reportengine: ftp'd 37 files in 0.73 seconds
Nov 20 06:35:50 raspberrypi weewx[2073]: cheetahgenerator: Generated 2 files for report SteelSeries in 0.78 seconds
Nov 20 06:35:55 raspberrypi weewx[2073]: genimages: Generated 11 images for SteelSeries in 4.51 seconds
Nov 20 06:37:48 raspberrypi weewx[2073]: restx: WOW: Failed to publish record 2016-11-20 06:35:00 UTC (1479623700): Failed upload after 3 tries
Por otro lado, estoy leyendo como os estáis liando con los protocolos.
WEEWX NO USA SFTP (el cual usa, por defecto el puerto 22), sino FTP o FTPS, pero no SFTP.
De verdad, que he dicho MIL VECES que la documentación de Weewx es mejor que la de cualquier otro software meteorológico.
secure_ftp
Set to True to use FTP (FTPS) over TLS. This is an extension to the FTP protocol that uses a Secure Socket Layer (SSL) protocol, not to be confused with SFTP, which uses a Secure Socket Shell protocol. Not all FTP servers support this. In particular, the Microsoft FTP server seems to do a poor job of it. Requires Python V2.7. Will not work with older versions of Python. Optional. Default is False
Como se puede ver en el log que he puesto, los detalles son pocos. De lo contrario el log sería ENOOORRRRRRME
Bien, pero para ver un log más extendido debes parar weewx, y modificar weewx.conf
# $Id: weewx.conf 2901 2015-02-05 21:15:03Z tkeffer $
#
# WEEWX CONFIGURATION FILE
#
# Copyright (c) 2009-2014 Tom Keffer <tkeffer@gmail.com>
# See the file LICENSE.txt for your full rights.
##############################################################################
# This section is for general configuration information
# Set to 1 for extra debug info, otherwise comment it out or set to zero.
debug = 1
# Root directory of the weewx data file hierarchy for this station.
WEEWX_ROOT = /
# How long to wait before timing out a socket (FTP, HTTP) connection:
socket_timeout = 20
# Do not modify this - it is used by setup.py when installing and updating.
version = 3.1.0
Arrancamos de nuevo weewx y comprobaremos el log.
Si no ves nada relevante ahora en el log, entonces, como dice Xavi, debes acudir al log de 1and1