Nice ones Vazgen! Redwater Den is an excellent idea.  I wanted to do the Thalmor Embassy too but it's not that difficult. I'd have to cheat my way into it too ..   

It seems like we have another Garret fan over here .

I'm going to record a Pinewatch heist myself, with some additional handicaps like no perks in Sneak etc.  I had one run in that place with Heavy Armor, 15 Sneak and one perk in Stealth for Tips and Tricks challenge once - the place is great for thieves 

Sunderstone Gorge is not that difficult if you get past those starting wizards 

It'll be quite difficult to pass by undetected the npcs in the tavern like room .

Yeah, that's the hardest part  I have a few tricks up my sleeve though 

Good luck with it! I'm looking forward to seeing it .

I'm also thinking of recording a run through Pinewath :D we could start a T&T Heist discussion/showcase..?

There was one already 

That would be great! We could make a list with all possible heist locations in Skyrim and include walkthrough guides (even videos?) for each.

That was a challenge Vaz. This could be more of a comparison between styles and different methods to do the same things :) I'm down of you guys are. Can you record vids Vaz?