Yeah, it is a bear to correctly solder the shield of LMR400 without damaging the foam dialectric. I only use crimp/solder connectors for this. Actually I solely use them now for everything because I've never produced a bad one, or had one go bad in use.
Do you have a dummy load? One is very useful for troubleshooting, as you can just walk the system backward until you find the problem.
One thing you can do is disconnect the coax from the radio, go up the mast and disconnect from the antenna and check for a short up there. If you have a break in the coax before going up the mast, then also check there.
If you need to replace the connector up the mast and are having problems soldering the center connector, there are center pin crimp connectors that don't require soldering. I'd choose the crimp/solder connector over that for more robustness, but it will work better than a bad solder job.
Mark