Hello there,
I see many answers to your question, but I want to say a few words on my own, as I have been there, done the same many times...
I purchased a 2020 Road Glide Special back in Dec 2019, have done several trips and enjoy it a lot.
I had a Challenger before, lasted only 6 months as it had a few issues that the dealer could not fix it and I was quite upset after spending 30K on the Indian.
I purchased a 2020 R3 GT a few weeks ago, I was dreaming about this bike since it came out, and finally I purchased it.
Now, I think the R3 is an amazing POWER HOUSE (no need for ECU tune at all), it is a VERY EASY bike to ride, it rides like a light 600CC bike, it is really amazing how it handles.
1-The bike has a few strange things, one being to start the bike, but you will get used to it, even though it is a BUSY system for starting up, could be simpler
2-Now I go my headlights flickering, trying to solve that problem, but it should be straight forward
3-After riding about 100 miles and if you get bumps along the way, you will feel the difference on the suspension of the R3 and the Challenger, cannot be compared, the R3 is quite hard in my opinion, hope I can make it a little softer (any inputs are appreciated it)
4-There is absolutely no wind protection for your body nor for your chest and head, I made a mistake buying a 46 inches screen from GP KOMPOZITE, they do not help much and they need to improve the alignment of the screws, TI DOES NOT FIT PROPERLY on the 2020 R3
5-If you will use for long trips, it will be a bit uncomfortable and gas intervals suck, as the tank only holds 6 gallons (I believe) which I get about 164 miles per tank, while I do 240 on my Road Glide (not a big deal at all, unless you ride long distances)
6-You will enjoy the LOOKS and COMMENTS about the R3, it is a freaking BEAUTFUL BIKE and it has lots of VERY SEPCIAL details that makes the bike UNIQUE, SO yes YOU WILL LIKE IT.
Thus, do not compare the Indian Challenger to the R3, they are completely different bikes, I wish you could just have both and enjoy both.
I am enjoying mine, but unsure if I would trade for my Road Glide or Indian Challenger today.
Cheers
Luiz