"... you don't want to 'teach yourself' with a skillset like that."
That's very true, maybe I should just throw my beginner's curriculum up here.
"varied skillset but of all the options I feel 'Wrestling' is my least well developed."
I think this is very common, but as you allude to, it has more to do with logistics than intention. It is hard to wrestle everyday, but much less hard to do BJJ or boxing, for example. There's something to be said about the ability to practice something with frequency.
I have developed some skills for takedowns but it's a strange mixmash due to how I learned it and practiced. my low single is solid, even goes to quite good if they situation is that they were trying to break free from a grapple and stand up I can cover the space they open so they feel they are safe and are not. I have gotten this takedown on significantly better werstlers then myself. I have an ok single in general my double is pretty crap to be honest.
I have some good trips/footsweeps and if it's in a gi I have at least a few options once I secure a grip. of course that is the trick lol
the thing is since I only have a few options someone only needs a few defensive pointers from a skilled wrestler or judoka to be "out of reach" as far as my takedowns go.
I really have no Judo or Sambo options where I live. It is actually difficult even just finding people willing to rep takedowns beause it isn't something they are as comfortable with. like if I want someone to rep sweeps with me I can basically pick my partner right everyone is willing but if I say something about repping singles holy cow maybe 1 in 20 are willing.....
I have a similar priority now too:
1)Low/Outside Single
No Judo options? That's some what surprising given how widespread that art is.
What about if you say "Can we drill this takedown I learned last week suuuuper slow? I mean, I have to go work tomorrow". There could be some tension because they have been injured doing takedowns, or they don't know how hard you'll go on your reps.