Forget GMRS, which are UHF, and go with VHF radios
Two way radios just won't work through several miles of woods. The only chance you have at all is to get a business license on a VHF frequency and get 5 watt radios. A repeater is a fixed station that "relays" your signal to the other radio...
Moto DTR550 worked very good
I had used Moto CP200 4 watt UHF on one cruise and they worked pretty good. On the next cruise I took the MOTO DTR550 and they worked much better. Amazing how 1 watt 900Mhz can outperform 4 watts UHF. The smaller (shorter) wave length just has a better bounce effect...
You didn't say what frequency you are on so I am assuming VHF. Have you considered replacing the pagers (as required) with a portable radio? The radio has a much better receiver with an external antenna so it just hears better. Plus they can talk back, not just listen. I sold the Vertex radios...
Wireless headsets
I can speak from experience as being a selling dealer of both Zetron and Plantronics equipment. Be sure all of your dispatchers are present at the training session on how to use the headsets. Proper use can create serious problems if not done correctly.
Many available now
I think all major radio manufacturers make LTR radios now: Motorola, Johnson, Kenwood, Icom, Vertex and other off brands. All, that I know of, that do LTR will do conventional.
Conventional repeater
If you run into a budget problem, since you already have some conventional UHF radios you could get a conventional UHF repeater with a multi-tone panel. Security and maintenance could use separate tones (private lines) and would not hear each other. As a two-way radio...
DTR vs. DLR
Besides the better antenna, the DTR radios have a much better receiver than the DLR radios which will increase the range. The DTR is a commercial grade radio and the DLR is a consumer grade radio. The DLR sure is cute and small and should be great for shopping, etc.
DTR radios work just fine
I agree with the others on using the DTR radios on a cruise ship. I don't think I went below deck 5 but it they worked great everywhere we went. Digital is amazing.
Motorola radios
I would start by replacing all batteries with new ones. A voltage that is too low can cause all kinds of problems. Be sure both radios are on the same channel and same code (all display numbers match). Good luck.
Vehicular repeater
The Vertex VXR1000 works great as a cross-band vehicular repeater. I sold a lot of them with no problems. Antenna placement on the vehicle is critical to prevent internal interference.
Vertex Standard | VXR-1000
The bandwidth does not have any effect on range. That is determined by the RF power output. The narrow band radios are required to turn the deviation (modulation to some people) down so not to "splatter" on the adjacent channel. You can still get the same audio out of a narrow band radio but you...
Consumers wanted frequencies that they could use without business/commercial/industrial interference so the FCC created the Family Radio Service (FRS). Originally this was not for business use but as time went on and the cheap price was too enticing it got out of control so the FCC gave in and...
Assuming there are no hills between each party to block the signal I would have to go with CB/SSB. The cost would be very economical and using SSB would give you more range with less frequency congestion.