For what is worth, I’ve narrowed down the problem to the well know Window scaling problem (RFC 1323 and
http://technet.microsoft.com/pt-pt/library/bb878127(en-us).aspx ). In fact, once I’ve disabled autotuning for this particular segment, Lansweeper started acting accordingly. We had already done that in the past on Windows Vista machines on that location but on a different issue so correlation was not apparent. When upgrading to Windows 7, that setting was lost (it is now on GPO, to not be forgotten again). As a reference, disabling autotuning is made via
netsh interface tcp set global autotuninglevel=disabled or
Computer Configuration -> Windows Settings -> Policy Based QoS -> Right Click: Advanced Qos Settings -> Inbound TCP Traffic is a set of levels that map 0 -> disabled. This is a workaround, not a solution - the real alternative was to change the VPN router on the site - the Cisco IOS version we're using there has no provisioning for Windows scalling. But that's another story....