I switched from a Spot Hogg Hogg It (5 pins) to a Fast Eddie XL with the double pin a couple of years ago. One of the first bucks I had an opportunity at was walking my way and I was ranging, dialing, he was walking, ranging, dialing, he was walking. I ended up not getting a shot (not because of ranging and dialing, it just didn't work out), but I learned that day that I needed to be able to shoot whitetails without dialing in 95% of the situations I would be in. Instead of dialing and shooting at 70 yards in the backyard every day for practice, I started shooting 20-40 yards with my double pin without dialing. My pins were 20 and 34 and I quickly had no issues using them out to 40 without dialing. I much preferred this method and have since felt much more comfortable in hunting situations when deer are around and have had no issues shooting deer this way. I am like you in that a deer at 35-40 yards looks like a long ways out and tiny, so those shots are going to be rare for me anyways. And if they do present themselves I will take the time to dial and make sure I can make a good shot, and if this causes me to not get the shot opportunity then that is ok.
I used the 2 pin in elk country just the same way, but I moved my pins to 25 and 37. I felt very comfortable to 45 on an elk without dialing. Called a bull in and killed him a 20 yards, but never considered touching my pins as he closed the last 50 yards.
At the end of the day, you have to decide what feels best for you and what you'll have the most confidence in. I tend to overthink things and stressed about this same thing when I switched from the 5 pin Hogg It, but haven't missed it one single day yet.