Ultra light backpackers have a creed, just like Socrates said "The unexamined life is not worth living" and the backpackers say, "The unexamined gear may not be worth toting" Unless you are doing a SOTA activation, your gear will not need to be evaluated down to the ounce versus value. But there are some lessons to be learned about evaluating each item and determining its usefulness, and possible multiple use. The goal is to be prepared with enough equipment with a reasonable amount of redundancy to be effective and not be overburdened with too much equipment. Preppers have the term "Two is one, and one is none". What are the choke points for failure in radio communications and how might we mitigate it?
If there is one law that is synonymous with Amateur Radio it is Murphy's Law. Interesting things happen to electronic equipment in extreme heat or cold. Plastic connectors will get cold and brittle and break. Lights will get knocked over and bulbs blown. And cables will get pinched in the door despite having the best aluminum chair holding it open. The goal is to evaluate the equipment and be selective about what is put into service where there may less than ideal conditions. Gear works great in the ham shack but put into the field and the stress of the enviornment will result in equipment failure. Select your best equipment for your goBag, inspect each item for wear or damage and replace.
Ask yourself what if questions. What if this item get's dropped. Or what if this item get's lost. Identify the most common scenario's and build redundancy in that item. A key thing to do is abandon your stock antenna on your HT if it is rigid. Replace it with one that is more flexible. The stiff antennas will not only break, but may break the connection inside your HT. And lastly test your selected equipment routinely in different conditions. An ounce of prevention in gear quality selection goes along way.
When we talk about redundancy, the term reasonable needs to be applied to the equation. Certain items in your gear may be too expensive or too large to have a spare. An example would be an generator, laptop, or HF transceiver. Some of these items redundancy can be mitigated. Instead of keeping a second laptop on hand for digital communications, have a jump drive with all the drivers and software needed for your setup so one can be borrowed. Other items are easily redundant. Having a spare rubber ducky, antenna cable, HT battery pack that accepts AAA or AA batteries is light. Having a spare HT would be ideal. Then identify all the accessories that can be shared between the two units. If you are using one mobile for voice, and another for digital. Ensure that you could swap the units in case of a failure of a data cord or microphone cord. Swap meets are a great cost effective place to find redundant parts for your equipment.
Another way to mitigate redundancy is identifying items that have multiple use. Have your headlamp and flashlight use the same common batteries as your HT. Keep your equipment to AA or AAA power source. The flashlight may be cool with the CR125 lithium battery but in a pinch it will be hard to find a specific replacement. You will be amazed at how many AA or AAA batteries you can round up by raiding TV remotes around the house.
Standardize Your Equipment
As much as you can, also standardize your equipment to rely on support of the Ham group or your neighbors. Keep your antenna connections to BNC for HT and PL-259 for mobile and HF. Power sources should be standardized to Anderson PowerPoles. I keep an clamp to Anderson PowerPole so any car battery can be called into service as a temporary source. Keep a small tool kit and solder gun in a bag to hopefully repair, splice, or will the equipment back into service.
Hopefully this gives you some idea's on not only preparing your equipment for service if needed. But also being reasonably redundant to stay on the air with Murphy's law looking over your shoulder.