Old school R.O.T. - Rule of Thumb for distance to the radio horizon (note: many newer VHF/UHF calculators use a slightly DIFFERENT calculator, mainly I suppose because they are strictly VHF/UHF) is:
1.415 X the Square Root of the FEEDPOINT height AGL (Above Ground Level) of the antenna = distance to the radio horizon. So, for example,
If your A99 is mounted at 25',
1.415 X 5 (which is the square root of 25) = 7.075, or roughly, 7 miles to the horizon. Does that mean you can only work a 7 mile radius? NO, because the OTHER antenna ALSO has it's OWN radio horizon.
So, if the station at the Flying J ALSO has an antenna at 25', then they too have a 7 mile horizon, which you must add to your OWN, for a total RELIABLE comms distance of: 7.075 + 7.075 = 14.15 miles RELIABLY (in the real world, these numbers may be assumed to be MINIMUMS, therefore, you are likely to communicate up to 50-100% FURTHER if unobstructed by hills, buildings, etc.)
So, to get @40 miles, two-way, each station will need radio horizons totaling (when added TOGETHER), 40 miles.
If, for example, you take your 25' A99 and move it to 100' and the Flying J stations does likewise, you are NOW:
Each at 14.15 to the radio horizon; and 14.15 + 14.15 = 28.30 miles. Given that the real world factors are 50-100% higher, you guys could therefore conceivably be 42-56 miles from one another and still communicate.
Now I realize that 100' is pretty much not 'doable', but perhaps 49 feet IS more of a real world height. If BOTH antennas get their A99's feedpoints (bottoms of the antennas) up to 49' AGL, the numbers would come out to:
1.415 X 7 = 9.905 miles X 2 (for both station's horizons) = 19.81 miles, which, in the real world, would probably give you guys 30-40 miles maximum distance.
So, BOTH of you guys need antennas at 50' or higher, if you want to make it "work."
Unfortunately however, the Flying J (as I understand it) is a Truck Stop, and as such, what we often find in Truck Stops is a lot of trucks with CB radios, some high powered, that you'll not likely be able to get over no matter how high you raise your antenna, you'll never develop the uV (millivolts) on the Flying J's receive antenna to overcome the near field of the many trucks transmitting (splashing/bleeding) on adjacent channels, not to mention electrical and/or impulse noises on his receiver.
My closest truck stop is only about 15 air miles away from me. My antenna (ABS1600) is less than 25' AGL at the feedpoint, and the truck stop (Imax 2000) is less than 50'. I have NO TROUBLE with them at NIGHT (when the skip is not rolling in and overpowering us), but have difficulty with hearing each other in the daytime. Our 'calcs' SHOULD be:
Me: 1.415 X 5 = 7 miles + Him: 1.415 X 7 = 10 miles = 17 miles RELIABLY.... but even still, since we're only 15 miles away, sometimes it works, and sometimes (i.e.: ionospheric propagation, local truck traffic, etc.) it doesn't. The fact that we have a Q-5 copy on one another at NIGHT, reinforces the validity of the calcs.