WA,
To answer your question about a transfer not beginning:
I know for a fact that some stations scan for more than one frequency for WINMOR activity. So the frequency you are trying to connect to may appear like it's a clear channel, but the station may be in use on another frequency. The very few times I haven't been able to connect to a specific station, I'll wait about 3-4 minutes and try again. But now that I think about it, that has to do with connecting to a station, not with the actual transfer of a message.
So you are able to connect to a station, but the message doesn't go thru?
Experience:
Yes, I use WINMOR every day now and really like it. I've sent HF emails via P2P (peer-to-peer), WL2K (various generic frequencies), and also posted messages on two specific BBS (I registered with the specific sysops to do that - a preparedness/prepper group called TAPRN).
I've been able to do the following:
send emails to non-hams (radio to internet)
receive emails from non-hams (internet to radio)
send and receive HF emails/messages to other hams (radio to radio)
send and receive HF emails/messages to hams or groups of hams on a BBS (radio to radio)
I keep meaning to try sending an actual file (attachment). Maybe I'll try that this week.
I've been successful on 20m, 40m and 80m.
There have been times when someone is too far down in the noise on the weekly prepper voice net (TAPRN), but we can always reach each other via WINMOR on those same nights of bad voice net conditions.
Also something good to consider - I typically use 100w for voice, but with WINMOR, I'm only using around 55w. If ya have to bug out with your emcomm kit and you are limited in alternative power, obviously using less power to reach the same contacts can be helpful.
FYI - Every night (I've been successful in the daytime too) I connect to one of the two BBS (for the prepper group) to check in and see if any member has left a message and/or send one to someone in the group.
Both BBS belong to members in the the same prepper group, so the sysops linked the two BBS together. That way, when a registered member connects to one BBS, they end up connecting to both of them, which is very helpful if they can only connect/reach one of the two BBS. One BBS is located in Maine and the other BBS is located in Oklahoma.
So imagine an example scenario - Prepper#1 can only reach the Maine BBS and he/she is trying to send a message to the other registered Preppers (who can only reach the Oklahoma BBS). Fortunately, Prepper#1 can do that because the two BBS are linked.
I'm lucky enough to be able to reach both BBS, but the messages seem to go thru a little quicker on the Maine BBS for me personally, so I end up using that one most of the time. I can reach the Maine BBS on the designated 20m freq, but the designated 40m freq is touch-n-go. For the Oklahoma BBS, I can reach it on the designated 40m freq but not much success on 20m.
Anyway, that's what I've experienced so far.
Sorry I can't be of more assistance on your issue of sending a message.
Winsatara