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802.1q concepts issue

Hi, I have read a lot of pieces on 802.1q however I am still perplexed as to the conditions when I should untag or tag a port!  Let me try and illustrate my confusion with an example, a switch and 4 VLANs (v1 to V4).

Port V1 V2 V3 V4
1    T  T  T  T       (HyperV server that uses all VLANs)
2    N  N  N  U       (A device that does not support VLANs)
3    T  T  T  T       (A router to manage security between VLANs)
T=Tagged U=Untagged N=No

My question is on port 2, I just have a device that I want to dedicate to V4 only however this should be accessible from ports 1 and 3.  What actually happens to traffic on port2 - will it append VLAN information Tag to it and will it be able to communicate with ports 1 and 3 if they are set to "Tagged" or should they be set to "Untagged" to match it?

What would happen if I have another device that did not support VLANs and this was on another port and VLAN for example,

Port V1 V2 V3 V4
1    T  T  T  T       (HyperV server that uses all VLANs)
2    N  N  N  U       (A device that does not support VLANs)
3    T  T  T  T       (A router to manage security between VLANs)
4    N  U  N  N       (Another device that does not support VLANs)    

Will this work?  Will ports 1 and 3 still be able to communicate with port 4 even though they are "tagged" and port 4 is "untagged" for the same VLAN?  Can I mix "untagged" ports between vlans or do I have to make sure all devices that do not support VLANs are on the same VLAN?!

Does the "tag" mean it is added as the ethernet frame leaves the port, or is it added when the frame is sent to the port?

I am very confused so any pointers would be great.
Thanks
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This question has been classified as abandoned and is being closed as part of the Cleanup Program. See my comment at the end of the question for more details.