Lots of folks can give good advice here but here are my experiences
I rarely shoot single shots off hand and am lucky to group 6" at 50 yards off hand. I spend a lot of time practicing and figuring out field shooting positions that work with the stands and blinds that I hunt from. This usually involves a bog-pod in some configuration right now. I try to put 500-1000 rounds down range a year on scoped contender/encore platforms. A 22lr or even better a 17hmr barrel are great for this. 17hmr is nice because you can easily stretch out past 100 yards to work on longer range shooting mechanics for cheap.
1) With scopes, proper alignment and a steady rest are critical. Practice helps a lot. I also find that quality glass makes a big difference with making a scope work well. Max range depends on how steady of a rest I have at the time. I routinely shoot 200m at the range off a bench and I am confident of bullet performance (hand load) to double that distance.

2) With a red-dot I have found that dot size and adjust ability of intensity are critical. I also found that I like some of the different reticle styles like the circle-dot ones. Makes it easier to acquire the target faster. With a 2moa dot at low intensity (no bloom or smearing) I can stack shots at 100 yards off a rest. I find this is highly dependent on the target you use. It's only possible for me if you can center the dot on a large target that you can clearly see. It's much harder to try to shoot the corner targets on a large sheet this way. Max range depends on how steady the rest is at the time. I routinely practice at 100 yards with this setup, but consider that close to the max range unless the situation were perfect.

As for field use of the above. I shot a nice buck at 100 yards with the red dot last fall. It was just after sunset and light was fading and it was definitely at the end of functional red dot hunting time for me with the low contrast shot presented. A scope would have given me 15 more minutes of time and much farther range but taken longer to get on target. I've started taking two guns to the stand with different sighting systems for this reason. Sit with the red-dot on your lap and leave the scoped gun beside you.

not knowing how/where you like to hunt, I would suggest that 7mm-08 is begging for a 2.5-8 or 3-12 pistol scope and the 10" 30-30 would work well with a low profile red dot at shots under 100 yards or as a brush gun.