A couple of initial thoughts on Till / Thompson just to start the discussion. Hoping this starts conversation on the below points since I'd really like to hear your guys' input.
Southpaw vs southpaw:
WB is a switch stance fighter. He can fight on either side but 90% of his fights are in southpaw stance. This might be because most of the guys he's fought are orthodox and he prefers to fight closed guard. When WB switches to orthodox, he's a bit more aggressive and throws more but also can get hit more. I'm not quite sure if this is a southpaw/orthodox preference or an open guard/closed guard preference. If it's both and he's best fighting closed guard and southpaw, then it won't be quite comfortable fighting closed guard and orthodox. I'll be very intrigued to see what stance and guard matchup he chooses here.
Distance closing:
In the past couple of years, WB has been most tentative against Woodley. Obviously because Woodley has a lot of power, but I think the other aspect here is that Woodley has that explosive first step and closes the distance. WB's success in the UFC has been due to pinpoint striking and an advantage when it comes to footwork. Not only has WB had the lateral movement advantage (see the first knockdown against Masvidal for a beautiful example of this), but also very clearly in the distance closing. WB can jump in and out so quickly that he can get his stirkes in and not be there for a return counter. Rory and Masvidal were able to tag him a few times but they weren't fast enough to really make him pay.
Though Till doesn't have as quick of a first step as Tyron, Till also is very good at managing distance and moving in and out similar to WB albiet with a less bladed karate style stance. Similar to how Conor pressures to draw out a counter, Till can get in your face, draw out a strike and then take a quick step back before jumping back in to land something. Till's timing has also been good enough to time simultaenous counters, stepping in with an elbow when his opponents come in. Now we're dealing with WB here who is multiple levels better of a striker than Tills previous opponents, but I think Till's distance game will be a bit more difficult to figure out than more stationary targets like Rory and Masvidal. WB will have to be much more careful exploding into the pocket with strikes because the possibilty of it amplifying the power of a Till counter.
Other factors:
Till is 25, Wonderboy is 35. With WB's explosive style, you'd expect him to slow down more with age than say a more grinding style fighter. This doesn't appear to be the case yet since he looked great against Masvidal. But there will be a time when age will be the limiting factor with that style. Maybe Wonderboy is a freak like Romero and can keep the ball rolling until 40, but I think it's more likely WB only has a couple of years left at the highest level. Fight with minimum 10 years age difference favor the younger fighter around 65/35.
Finally, Till will obviously have the hometown advantage whereas WB will be fighting for the first time outside of North America.