In my case, WeeWX in RPi and NAS web server (Linux to Linux). Instead of having extra service running, checking and sending, I created a NAS share folder into RPi, and WeeWX writes direct to it. That is, WeeWX "sees" as a regular (mounted) folder in RPi, but it is in fact remote in the NAS.
Never had problems and always there.
As mentioned by Greg, I assume the same can be accomplished through Samba for Windows.