You get what you pay for. If you don't do more than a couple dozen a year it's a balance between function and budget.
I use these
Greenlee CrimpALL Crimper Frame Only, Series PA8000 - - Amazon.com (or the Paladin equivalent) with replaceable / interchangeable dies. The dies are pretty standard and should work between crimpers from different manufacturers. I have two handles in my coax box so i don't have to change dies often, but then again I buy connectors by the gross. When you aren't crimping coax use the wire crimper dies for ring terminals and splices- they are head and shoulders above the wire crimpers you buy at Lowe's. You can get combo dies in just about any set of diameters. Be forewarned that each connector type and manufacture may have a different spec.
Stay away from single size coax crimpers with fixed dies unless it fits the budget and you don't use them a lot. Once over-tightened and sprung they're worthless. The high-end frames have adjustable stops- one of mine is over 20 years old.
Putting a connector on coax is really two separate functions: Mechanically keeping the coax attached, and minimizing RF loss. Doing both requires dollars, and there are often cheaper ways of doing it. I would put my emphasis on the RF side if you have to make a choice.
For flexible coax the attachment to the connector isn't going to survive much tension pull any way you do it. You need to secure the coax before the connector to keep it in place. If a sharp angle at the back of the radio is an issue buy a 90 degree adapter or put a 2" rubber boot on the coax and slide it up to the connector when it's installed.
For transmitting UHF and 800 I prefer solder, but haven't been able to prove that it is much better. VHF doesn't really care (at least 50 watts and less). 2.4G is a definite solder for smaller diameters, but there are many styles of non-solder connectors that seem to work just fine with LMR400 in all bands. Adhesive-lined heat shrink is your friend.
The N-family (N, BNC, TNC, etc) has less impedance miss-match than UHF-style because the diameter ratio remains constant. That said, Mother puts mini-UHF connectors on everything mobile. Kenwood puts N's on their 800 models.
You are, for the most part, dealing in the final 2% of signal improvement. You need to ask yourself if improving 98% efficiency is worth spending a few hundred more dollars.
