Would you say dialing in the TM36-68 would be a bear, same, or easier than the stock carb on stock-bore, uncorked, @5000' asl? (The BB 33/34 is out of my price range so looking at the TM36-38.)

 

Both have been done many times, and either should be fine if you just follow path trod by others.

On the stock carb it basically boils down to the pilot jet, the main jet and the needle. Pretty much that what most people do. You can get away easy and cheap. CV carbs are by their nature pretty forgiving.

Here's my, very common, formula for the stock carb: 38 pilot and a 132 main on the N1TC needle. 2 clips down with the air screw at 2.5 turns out.

The TM36-68 is more or less also plug and play if you copy someone else's jetting that has a setup like yours. This said the TM will have a needle jet, pilot, main and air jet, plus timing for the pump so there are more variables.

You will not go too far wrong with this setup in the TM:Pilot: 17.5 (VM28/486)
Main: 130 (N100.604)
Needle jet: 568 series P4
Jet needle: 9EBY01-50 – clipped in 3rd from the top