I do like Toscano cigars in the pipe, for example, and if I feel like a Vanilla tobacco, my favourite is a Toscanello Vaniglia. I cut a third off (a Toscanello is half a Toscano, and has a weight of about 4g).
I then break the wrapper sidewise open (that way it gets a bit more loose), and push that into the pipe like a flake. It can be smoked very slowly that way. One third (appr. 1.3g) in the pipe lasts as long as a whole Toscanello smoked as a cigar. And is very flavourful. Rubbing the filler out works as well.
If I find cigar tobacco too alkaline for the pipe, I do the following:
# Take, let's say, 5g of cigar tobacco.
# Fill 5ml of rum or whisky into a small "Schnapps glass".
# Add 1 drop of good, pure anise seed oil or star anise oil to the rum (20 drops would be 1 gram from my anise bottle, so 1 drop = 0.05g or 1% of dry tobacco weight).
# Press the tobacco into the "Schnapps glass" and let steep at least overnight, then dry out.
The anise will add just enough sweetness, offset the alkalinity and reduce nicotine availability. Licorice extract works as well.
Adjust the amount of anise to your taste (but careful, it's too easy to add too much).
You can also cut cigars into pieces, soak them in that liquid, dry them out over several days or in the oven and break the wrapper open sidewise to use as a flake.
Cocoa powder (1-2% of tobacco weight), vanilla extract and other essential oils (i.e. orange or lemon grass) can also be added with sweetening/smoothening effect. Tiny amounts have a big effect.
5-10% invert sugar should do something similar, but I don't like it as much. Anise nicely underlines the cigar character, while, in my experience, invert sugar somewhat flattens the taste.
