Very happy to hear all this :) Great work on your voice. Girlfriend sounds like she is well broken-in ;)
I've never gotten into it with enough frequency to see this myself, but I've had some pals tell me if you give a girl anal enough, she eventually reaches a point where you can basically just pop it in and go (with lube... although I've seen a few guys claim past a certain point you do not need lube. Not sure what they are doing there / what that is all about though). Presumably that would only be once she reaches the point where she has such strong positive anchors to it her sphincter starts opening up at the very thought of your cock going in...
Re: freelancing -- I will just say, that among the middle tier and top, for pretty much everything, there remains a huge dearth of highly skilled freelancers. I do a lot of hiring and at this point I will usually hire four people to every job, give them all the same trial task, then evaluate them against each other to find the best. Even with hiring the best candidates, usually only one or none of them is seriously good. Numerous times I have done trial jobs, hired four people who seemed high-skilled, and wasn't satisfied with any of them.
The bottom is definitely crowded. The middle less so. At the top tiers of any skill even moderately in-demand skill set, however, it is definitely a seller's market. There's a lot more demand for high-skilled freelancers than there are freelancers to meet that demand.
Keep raising your skills in Python and copywriting and you'll reach a point where you can't beat the offers back with a stick. Quite possibly before you even reach an "advanced" level with either (though you should keep improving anyway -- especially if you want the highest money-earning gigs with the best-to-work-for clients).
Good luck, man ;)