From following Tim's twitter... It sounds like he had multiple families approach him near the Jungle (Jingle) Cruise while shooting his Christmas Updates Vlog. That caused a group of people around Tim and that sent Disney security into 'Meet Up' dispersement mode.
As mentioned above - 'See Ya Reel Soon' was scolded a few years ago when they had a low key meet up in the parks, so it has long been policy to not hold events in the park without Disney Authorization. This is mainly because Disney can charge a hot $$$ to groups who rent areas of the parks out for events.
I think you are fine to take a photo with Tim, but don't approach if a large crowd is forming.
My question in all of this is HOW does Lou Mongello do monthly meet ups in the parks? It looks like he does them in quick service places where it could be considered friends getting a meal together? Not sure there. I've asked but not got any reply.
As for Tracker's income... Tim and Jenn are both full time youtubers now. Tim had been low key about his former job because he worked with children and didn't want any crazies to interfere with that workplace. Over the summer their
YouTube earnings spiked and they were on track to make almost $300,000 from the channel. However... YouTube is constantly revamping their monetization policies, so their actual income is far less than that off their main channel. Tim and Jenn do have some other YouTube channels that bring income as well (MyThemeParkPOV) but they are doing well for a 'normal' family and that is why we have seen the home renovations and new car purchase. However - Their home (which is not in Orlando) is fairly modest compared to most of the country.
I think Tim and Jenn deserve every dollar they get form YouTube. They have been posting daily for over 6 years now... They have created a brand and they should be rewarded for it by all the T-Shirt Sales and ad revenue from YouTube.
They are invited to some events as 'media' - but for the most part... They pay out of pocket for most expenses (see recent
Disneyland trip), and being self employed - 25% of the revenue goes directly to the government. So the '$300k' is nice, but they are by no means rich.
The sad thing about all of this is how mean the internet is towards 'internet celebrities' - They are trolled very often on Twitter and people set up accounts that reveal their real names and actual address. They downplay this often, but I know that it has got to send up red flags for security and safety with these stalkers.
Big lesson here... Respect. People on YouTube and TV are real people... they have feelings and the trolls do hurt.