First, about the intermittent difficulty connecting to the CWOP servers. I had to roll-back from WL 5.9.3 back down to 5.9.2a-beta because I was getting a lot of those. There seems to have been a problem with a couple of the host/servers and 5.9.2 was timing out. In 5.9.2a-beta they shut off the timeout, and in 5.9.3 increased the timeout time (speculation). But there was still one server that would just take too long to respond and 5.9.3 would throw that error. I have not had that problem again after going back to 5.9.2a-beta. There is a sticky-thread in the CWOP forum here with links to 5.9.2a-beta if you want to give it a try.
Second, about no barometer data. That might require a more experienced user, but here is my observation. Your raw APRS packets don't seem to have any baro data, so it is not leaving your pc. You say it makes it to WU, so that is where I am uncertain. Here is a peek at one of your raw packets and one of mine...CW9576
My only other shot in the dark is to ask when you registered for your CWOP ID, if you are just now starting to upload data. Your number (CW9576) looks like it was registered a couple of years ago maybe, compared to mine (DW6891) as registered this January, so I was wondering if you had just recently registered it and it should be "DW" instead of "CW" for any reason. The lat/long/elev for the REGISTERED (with russ chadwick, not from your station packet) gives them some reference for what they expect to see (especially barometer) so if you are uploading to someone elses ID, I have no idea what results might happen. You can double-check the registered lat/long/elev on the gladstonefamily.net wxqa page. Your link would be http://weather.gladstonefamily.net/site/C9576
but it shows "station not found" so something must be up. Since you mention Russ Chadwick, I am assuming you sent him an email letting him know you registered for a CWOP ID and that it is sending packets? I don't know if Gladstone gets your data before then.