From my experiences in using a simplex in semi wooded to heavy wooded areas is about 1-1 1/2 miles. Usually wooded areas having rolling grounds which brings an unwanted element into the scenario, these guys can not give you a straight forward answer as the variable changes for every environment or topography base area you enter into. My strong advice for you is that if it intend for field deploy ability simplex family communications take this route. Get either a tri-square radios for heavy commercialized areas or hot spot travel zones. If its wooded area, camping etc go with you maximum wattage achieved able on a radio (4 to 5 Watts) on GMRS. You can always introduce a repeater on gmrs later if you would like. Nowadays portable two way radios are fairly easy to obtain and program for GMRS repeater access. Plus, depending on what repeaters you purchase they can be relativity cheap for what you want to do and adequately small.
The most important rule, that I think was hit on here in a little bit is height. It's not so much the wattage or the gain as it is the height. The gain allows you less signal distortion and better penetration in and out of buildings. The other thing not mentioned is signal loss distortion which will effect your gain and your power out at the antenna. Not the power out at the box.
Simplex-
in picture format
Point A can hear and transmit to both Points. Point A acts as a repeater and transmits out as far as his/her radio allows for penetration from wattage out and proper gain at proper height. Point B and C get blocked from talking to one another by building, foliage-ie hills, trees, etc. No, structures or foliage blockage Point A transmits out farther, ie-tree stand would be a good example of this, however B and C can now talk to each other because nothing is blocking them, allowing for wider area of radio coverage by portable.
If the person is on the opposite side of the wall or sightly pasted the exterior wall they may be able to hear the traffic. Other rules of thumb, more wattage equals better punch through buildings-misleading. Localized areas the theory is correct, communications on the edge not so much.
This is the power theory, whats not taken into consideration here is height or gain. Another critical factor that is pasted on in small installs is proper grounding skills.
5 watts out 2-1/2 miles of coverage
4 watts out 2 miles of coverage
2 Watts out 1 mile of coverage
1 Watt out 1/2 mile of coverage
bubble packs .500 mill watts you figure out..... (not all bubble packs are created equal)
110 Watt mobile to mobile 55 miles of coverage
50 Watt mobile 25 miles of coverage