Stir together the flour, cream of tartar, baking soda and salt in a medium sized bowl. Set this aside.
In a larger bowl beat the softened butter on medium to high speed for 30 seconds.
Add the granulated sugar and beat until it turns creamy and smooth. Occasionally scrape down the sides of the bowl.
Beat in the liqueur or milk if using, and the vanilla extract.
Next, beat in the flour mixture until everything is combined.
Once combined, cover and chill the dough for 30 minutes.
Remove the dough from the fridge and divide into two equal portions. You may want to use a scale for this.
Roll out each half into a 12 inch rope.
Wrap up each roll in saran wrap and chill for about 4 to 24 hours.
When ready to bake, preheat the oven to 375 degrees F.
Line two cookie baking sheets with parchment paper. If you have four all the better.
Slice the rolls into 1/8 inch pieces.
Place 50 lollipop sticks about 1 and 1/2 inch apart on your prepared cookie sheets.
Place a dough slice, centered on one end, of each lollipop stick.
Bake for about 6 to 7 minutes or until the edges are a light golden brown.
Bake the rest of the cookie slices without the lollipop sticks.
When ready, let the cookies cool on the baking sheets for one minute, then transfer them to a wire rack to cool completely.
Meanwhile, prepare the buttercream.
In a medium sized bowl, beat 1/2 cup of softened butter with an electric mixer on medium-high speed for 30 seconds.
Beat in 1 cup of the icing sugar, raspberry jam and the liquor (or milk).
Gradually beat in the remaining 1 1/2 cups of icing sugar.
Spread about a teaspoon of the raspberry buttercream on the bottom part of each cookie with the stick.
Top with the remaining cookies bottom side down, pressing down gently to sandwich together. Set aside while melting the chocolate.
Melt the chocolate in a microwave safe bowl on 50% power for 1 minute. Stir well and continue to microwave at 30 second intervals until smooth and completely melted.
At this point the candy melts will need to be thinned in order to make them more fluid and not overly sweet.
Stir in some vegetable oil, 1 teaspoon at a time making sure it is well incorporated. ( a good rule is 2 teaspoons per 12 oz of candy melts.) It should give a ribbon like pouring consistency.
Pour the melted chocolate in a wide rimmed coffee mug. Stir again.
Hold each cookie pop by the stick and carefully dip into the melted chocolate to coat all over and let excess chocolate drip off back into the mug. You can also tap the cookie stick against the rim of your mug to help it along, turning the stick over and over as you tap. This helps to achieve an even coating.
Place on a waxed or parchment lined baking sheet and sprinkle with funfetti.
Repeat with remaining cookie pops.
Keep them flat on baking sheet till chocolate is set.