One of the youtubers I follow is LegendofTotalWar - he has two series that are sort of in this vein: Saving Your Disaster Battle and Saving Your Disaster Campaign - where he solicits save files from his audience that contains games in dire straights (either tactically a very bad battle is happening in an otherwise decent campaign or strategically a campaign has gone really wrong - and also some battles are going terribly). He uses both of these to produce long form content of him walking through the fixes by hand since he will almost never naturally get himself into these terrible situations on his own due to his experience - but these experiences are much more likely to be common to the audience compared with stomping around the world like a mad man. The thing is, though, that these are content productions for him - he will send the fixed savefile back to the submitter but he isn't just doing it as a hobby, he's finding a creative way to generate more content for his channel.

He gets an awful lot of submissions for SYDC that are very early into the campaign and involve the player overexpanding too quickly leading to general instability and kingdom poverty - guarding those immense borders requires an economic engine that you just haven't gotten running yet. He will often pass on these submissions because they come in quite often - and this is where I think your proposal falls down.

The people producing really high quality instructional content have invested a significant amount of time in refining their presentation and editing skills - in addition to their chosen profession. Most of them can make more money and work more efficiently by broadcasting their content en masse to a wide net of listeners. Getting them to talk to someone one on one is likely going to be a significant paycut for them and considering that nearly everyone has the same issue they're not going to be able to re-sell those consultation hours to others - occasionally sure, they can record them fixing the issue or talking through a diagnosis - but often times it's going to be the exact same story.

So while I may be delighted personally if I were to receive legal advice from Devin Stone (aka LegalEagle) there are a lot of quite capable lawyers that can handle my legal issues on their own at a much lower rate - not because Mr. Stone would look to exploit me price-wise but because he can be doing much more valuable things with his time.

I feel like this business would end up in an awkward spot where it would attract a large number of mostly unknown professionals and quite quickly price those professionals out of its market by giving them a publicity boost that drives up the rates they can and should command. I think, by definition, you're not going to be able to afford to hear from the person you value most due to how much everyone values them and how valuable their time ends up being. But hey, if you are ever able to put me on the line with Rasmus Lerdorf when I'm really grinding my brain on some hard PHP code I'll sign up.

Oh also, creating a sense of celebrity and then allowing people to communicate privately with those celebrities is likely going to bring out a lot of really creepy stalker folks - I feel like you'll have a very high risk in trying to support and protect your professionals from e-stalking and overt sexualization.

Lastly, I wanted to clarify that I'm really not trying to poop on your idea at all - this is meant to be constructive criticism. I do hope it helps and I'd be happy to answer any questions if you have more.