4 isn't really that many if you have difficult terrain to overcome. Yes, it's an investment, but if it's useful to you, who cares. Now, having 4 tower leases, or even have someone willing to lease you tower space, that's the impressive part, considering crown castle won't even return a phone call.
Yea, all my LiFePO4 batteries are bioenno, and I bought their charger with the battery. They do stop charging (LED goes green from red) when the battery is full.
An external antenna would probably remedy your solution over an HT in the car. Doesn't matter if it's the same frequency, other electronics tend to not like transmitting anything near them. Computer screens, computer speakers, etc. all complain when even 2W of VHF, UHF or 6meters is transmitted within a few feet.
Not when the radios themselves are 20+ years old, and were first programmed with a true serial port.
I can't remember if the TK-880 needed booted up in a programming mode or not. I guess check the manual to see? That may only be for firmware updates though.
You won't find them new anymore. TK-3140 was a great Kenwood that has Part 95 certification. They used to be $70-110 used, I still have a handful of them, used the KNB-55 battery, which is also used on the NX-3000 radios.
These guys check the radios out before selling them, for $150 its fits your budget https://used-radios.com/kenwood-tk-3140-uhf-450-490mhz-250-ch-4w-portable-radio/?srsltid=AfmBOor3hXfzNg6frpl6zsTfAzixQGKZJjih1N4fJGGRJn8_YKKdad4w
This all depends on what and how tall you plan on using the antenna. Simple is a 1/4 or 1/2 wave whip with a ground plane kit, can be broken down quickly, and have the least problem with wind. A fiberglass antenna could be used as well, anything 4' or less would be ideal for packing and hanging on a telescoping mast. @marcspaz has a portable go kit with guy wires, he's posted it here a few times. It's a bit of work to balance portable and effective.
Have you tried running KPG as an administrator? I've also had issues at times that a reboot of the system was required to clear all com ports of previous use.
open device manager, see what port the cable is. I can't remember if KPG-49 limited which com port you can use, you may have to reassign the cable to a port 1 thru 4. You also have to set the com port in the software.
I did a handful of contests when I started out. One was field day when COVID was still a think and everyone worked from home. Beyond the difficulty of figuring out how to get the radio and logging computer on a generator to work 1E, and the 1 RTTY contest I did, contesting in general has lost my interest. I barely get a chance to jump on HF, and usually when I do it's FT8/4 so I don't have to talk to someone.
Is it possible? Yes. Is it practical? No. It could be achieved if you have enough tower height and plenty of filtering. You would have 2 "repeaters" at each location, 1 would be the repeater, the other would be a "fixed station" and have to follow those rules. The fixed station would be a duplex RF link between the two repeater sites, but you would need to use directional antennas and significant physical vertical separation from the repeater antenna and the link antenna. Likely you would have to run the link and repeater as far apart in frequency as possible, repeater on 15 and link on 22 or the other way around.
Can it be made to work? Probably. Will it be expensive? Yep. Will it be worth it? Not for the average person.
Install it in a permanent manor such as a center console or hard mount under the dash. Don't leave HT's visible. That's the best you can do.
In my wife's car, everything is mounted in an overhead shelf, can't see any of it from outside, but you do notice the antennas. When parked for a week somewhere I pull the antennas and put NMO caps on so it's not a target.
This is probable for many of the ham or single band antennas, but some of the magic in the "all-band" HT antennas doesn't appear to be improved by a tiger tail. Though, to be honest, the radio bodies are significantly larger and involve much more metal than say a FT3DR or Woxun GMRS radio.