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NASA sent video 250,000 miles from the moon using 3W of RF. Line of sight is the biggest thing about UHF. If the OP's friend had LOS to the repeater, 80-150 miles from a handheld is perfectly capable. Also, it would surprise most to know that the radios used in aircraft are generally 10W (AM) radios. Though transmitting in the lower portion of the VHF high band it is still based on LOS communication principles. Sent from my iPhone using Tapatalk

radio test. LOL https://youtu.be/kZCDBsBuhmg

The long and short is yes UHF can travel hundreds of miles with clear line of sight. Satellite Communication for example most often operate in U/V mode. meaning that pending what country made the satellite it will transmit in UHF mode and Receive in VHF mode. they typically are less than a full watt of power, something between the order of .2 watts to .8 watts. you can listen to satellites like SA-50 on a Baofeng handheld with the squelch open. now if you have an Arrow U/V weak signal antenna you can really get out. As far as "repeater Skipping", i've never even heard of that. im not sure what you mean by it. The theory id have is if he has a 25 or 50 watt mobile and you are high enough or the repeater is high enough and far enough out, you could transmit 80 plus miles away to "that" repeaters freq's for that local area and then that person would do the same. Im not sure what you mean by "repeater SKIP". out here in nevada i can take a juentai 6188 with a jpole and transmit to ELKO NV over a mountain range to the repeater in ELKO on UHF. I don't hear the repeater keying up, but the hams there can hear me and they Transmit to my repeater out here via tone patch to a VHF repeater. radio waves travel farther than you think. and UHF and VHF pass through the ionosphere which is why you can use a radio like a baofeng for Satellite Communications. As far as nothing on GMRS goes, that could simply be no one on the air or not used to much in your area. or something else to remember, you are a licensed GMRS USER NOW, you are allowed to operate to 50 watts. most folks do not have licenses and buy the bubble pack radios that are 1/2watt with a ridiculous rubber duck that probably wont do a mile. something to think about. Everything comes down to ANTENNA's with radios more than power. i've talked some 30 miles away to reach a repeater on my UV5R with a NA-771 anteanna on LOW POWER simply standing in a position the signal could pass between. just remember your signal cant be blocked. if i took my UV5R to a city i bet i'd probably not get a mile. with all the stuff in the way to block it. ALSO the radios you buy in walmart etc will not allow repeater connection!! so there could be a ton of people using bubble pack radios and you'd never hear them unless they were very close by. I use the satellite commo as an example of how far a 1 watt radio signal will travel. Most satellites are 150 to 400 miles up and you can reach them with a handheld and the sat's have a max 1 watt receive limit! most of them. so dont think your radio "whatever it is" wont do it. just think antenna!!