Find yourself a high building or mountain nearby (< 1km with laptop) and try to see if you can see the antenna's again. If yes, you saved yourself a climber, you are just overshooting at close range. If no, you can still arrange a climber to check everything.
Did you made the N-connectors fit to the LMR-400 cable yourself? Or do you use prefab? The last is usually tested and if the length is correct the preferred use. But often you need (or to save a bit on the costs...) to adjust the length of the cable to you needs. Meaning you have to put the connectors yourself. In this case google on how it exactly needs to be done. It is very easy to do it wrong, specially if you don't really understand what the purpose of the several parts of the cable and connectors are really mend to do. Creating a wrong connection that destroys the radio-cable-antenna chain is so much more probable than doing it right straight away. It definitely needs some experience and skills .... I have been there myself...
And to make things worse, you have at least 6 points of possible failure if we only look to the connectors.......