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Sending pristine CW over the internet during contests at remote stations is one of the greatest challenges of remote operation.  The first way I tried, and the method I still use for basic iambic key sending direct from the control point is via the internal system of RemoteRig.  That system also allows for direct 'on-off' keying that is generated by programsl like N1MM Logger+, and it works...most of the time.

For contests like ARRL CW Sweepstakes,  'most of the time' is not good enough.  Letters get hammered when packets get 'busted', Also latencies can change dramatically over the public internet.   In order to hear what you are sending, there can be no latency from the key to your ears. so you listen to a local tone.  The result is that true QSK is not possible. 

The public internet does seem to support remote desktop options like Team Viewer and VNC, and any latency in the visual application is not a significant problem.  The latest solution I'm testing now is running N1MM on the computer at the remote site.  I added MicroHAM's MicroKeyer to the mix to send WinKey data from N1MM and the initial testing shows it works since all CW sending generated by N1MM, which is about 99% of sending in a contest, originates right at the remote station.  The only thing that runs over the internet is the F-key data that I trigger with the remote desktop software.  The iambic key is still connected through RemoteRig and is good enough for the few times I use it during the course of a contest. 

In the 2020 California QSO Party, I was given the special event call K6O as part of the Northern California Contest Club's 'SEQUOIA' promotion which gave an award to any op who worked enough special event stations to spell the word 'Sequoia' with the last letter of the call.  I was one of three 'O's' which caused pileups on both phone and CW.  Things went great for about two hours, then the dropouts started, and they got worse and worse until I had to finally quit the contest.

I was so frustrated that in the following weeks I reactivated a 440 MHz, FM audio link from the remote site to home.  This consists of surplus, but very high fidelity equipment that had been used by broadcast stations for sending audio programing from remote locations such as shopping malls news scenes around town.  Originally designed to operate from 450 to 455 MHz, it was easily converted to ham band use with a new crystal and ID'er to send my callsign every 10 minutes.  It works like a charm and is unaffected by the foibles of Xfinity!