I never advocate an amp over a good antenna but someone needs to flaunt their knowledge.
Let's change the way we look at a radio signal from expressing it in sheer watts to expressing it in DB - since any RF engineer you talk to is going to explain it to you in this manner.
The radio as you like to call it will be called the Generator, and the antenna will be called the load. In theory, if the load matches the generator, all of the power applied will be adsorbed by the load and radiated. If dealing with a mobile, we won't worry too much about loss, since there is not a lot of loss in a piece of coax 20' long.
The greatest gains are between 3 watts and 500 watts since 3 watts is enough power to radiate a good signal and can easily be converted into Db.
When referring to Db we either have to use the term DbM or DbW =- dbm being decibel milliwattt, dbw being decibel relative to one watt.
In theory, Mr. Collins devised a way to express gain linearly using a scale of 1 - 9 and then 10/9. Each number increase from 1 to 9 represents a 6 db gain in signal strength. After S9 signal strength increases 10 fold.
To increase signal strength we need to increase power or radiated power or move closer to the source.
A true 1 s unit RST gain requires a increase 4x or 400% in power.
A 10 decibel increase in power requires a power increase of 10 times.
Using 3 watts as a example with two identical dipole antenna's
S-5: 3 watts
S-6: 12 watts
S-7: 48 watts
S-8: 192
S-9: 768 watts.
If we use a more efficient antenna and we can increase our perceived transmit power.
S-7: 3 watts
S-8: 12 watts
S-9: 48 watts
10/9: 480 watts
20/9: 4800 watts
Using a 25 watt Ranger 2950 - we could expect a signal report of about an S-6 with the 4 foot whiles, while we could expect a S-8 to S-9 signal report using the Solorcon A99 antenna @ 30' above ground...
The Solarcon A99 would have at least a 12 Dbd ( decibel over dipole ) gain over the 4' whip.
Again, it is all just using what you have more efficiently.
On 11 meters I would use signal side band, not AM and I would use two Solorcon A99 antenna's and two masts 30' or more long. You could attach them to the side of your truck - since you already referred to 4 foot whips on headache racks.
If both trucks were at the highest points, this would probably get you 20 miles in any one direction..
Once you get above S-8, there is no reason why two people shouldn't be able to hear each other, as long as you pick a clear frequency.... Avoid any channel below 30 and you should be ok...