Zero "skill" is needed to work a DXped or DX during a contest on CW. Install CWDecoder on you PC and then program your call in one memory of your IC-7300 and 5NN TU in another.
I've yet to see a CW Decoder that's more than "very casual" help, at best. I love operating CW, but I cannot run in that mode. I can do assisted S/P pretty and scour mults really well by ear but couldn't run in a DX CW contest if my life depended on it. That skill is the difference between great CW ops and guys like me. I freely admit my code sucks and will
always suck, but it's just so enjoyable to do, even knowing my skill limits.
I keep CW GET running in a window but it's more useless than useful. Occasionally I will be able to look and see a missed exchange or a callsign my brain just went
tilt when trying to copy, but otherwise decoders are laughable when signals are marginal.
When I first started getting serious about CW contests the best tool I found that enabled me (and probably thousands of other crappy CW ops) to operate CW contests competently was ESM mode in N1MM. I don't have to worry about a suddenly sloppy fist, but when it comes to calling in the proper time and getting the speed just right what I find today works better is having N1MM set to 35 WPM, and my paddles set to 25 to call slower stations.