Knowing your gear is to trust it
Trust comes from knowing something. The more familiar you are with something, the more second nature it is, the more you trust it. Once you know each feature, each little nuisance, you can use that piece of gear or software almost without thinking.
Take my GORUCK GR1 for example.
The GR1 has been paired down to the simplest it can be. Each feature has its purpose and there is nothing there that is redundant. It is also built to survive. Because of this I was able to learn each and every feature fast. I used this ruck on the field and under fire, rappelling off a roof, during the grueling GORUCK Challenge, and countless other occasions where simplicity and usability were paramount. Having a piece of gear that performs every time, that it's easy to maintain and is durable is key, in my opinion, especially if this gear is going to be used on stressful situations or when lives are at stake.
The same applies to software or digital tools.
I'm a big believer in single purpose tools, the UNIX way. Have simple tools that can be used together to provide the best service there is. Having the possibility of feeding the output of a program as the input of another is a great feature.
Simple software is easy to learn, easy to work with and easy to fix. Simple tools can be used under stress as well, or when speed is key. So, instead of choosing your next tool based on the number of features it can provide try to check what is the tool's purpose, what does it offer as it's most relevant feature and whether it does this the simplest way possible. Build your tool's arsenal based on this.
An example of this is Notational Velocity.
Notational Velocity is a simple tool with the sole purpose of taking notes. It's extremely good at it. The interface is simple, fast and without any fancy elements. It's easy to learn.
Next time you are trying to figure out a piece of gear or tool, think about what you need first, what is the purpose of this new tool, then choose the best quality you can get. Get the best you can buy with your budget.