Today, we delve into the labyrinthine world of venue booking software, an area teeming with complexity as it balances a myriad of factors including user interface design, functionality, security, and customization features. The selection of a venue booking software is a critical process akin to a symphony conductor choosing the right orchestra - a misstep could result in a cacophony rather than a harmonious performance.

To navigate this complex landscape, one needs a compass, a set of pertinent questions to guide the selection process. These inquiries target the critical components of a venue booking software and ultimately help in identifying a system that will perfectly align with your event's needs.

• Firstly, consider the software's functional scope. Will it merely serve as a venue finder or can it also manage contracts, billing, and event logistics? The Pareto Principle, or 80/20 rule, suggests that 80% of the output results from 20% of the input. In this case, 20% of the software's features will likely deliver 80% of its usefulness. Identifying these essential features is crucial.
• Secondly, delve into the software's scalability. Can it adapt to handle increased capacity or scope in the future? This idea is rooted in the concept of economies of scale, a theory derived from microeconomics. An efficient software will provide increasing returns to scale; as the size of an event increases, the average cost per booking should decrease.
• Thirdly, assess the software's user interface and user experience (UI/UX). This dual facet plays a significant role in ensuring smooth interaction between the user and the software. While UI is the graphical layout of an application, UX involves the user's experience in interacting with these elements. Good UI/UX design can greatly enhance the software's efficiency and effectiveness.
• Next, turn your attention to security features. In a digital age where data breaches are commonplace, it is paramount to ensure that information stored in the software is secure. This links to the law of probability, an important theory in statistics. With each additional piece of data stored in the system, the likelihood of a security breach theoretically increases. Thus, it is critical to ensure robust security protocols are in place.
• Fifthly, assess the system's capacity for customization. Can the software be tailored to fit your event's unique needs? The relevance of this aspect is highlighted by the Nash Equilibrium, a game theory concept that suggests the best outcome occurs when each player in the game has chosen their strategy, and no player can benefit by changing strategies while the other players keep theirs unchanged. In this case, the software should allow you to modify your strategy (customize features) to achieve the best outcome (successful event management).
• Lastly, ponder over customer support. Will there be assistance available when troubleshooting or if things go awry? This component echoes the concept of opportunity cost from economics. Time spent grappling with software glitches is time taken away from other productive tasks. Thus, an excellent customer support system is crucial.

These questions, while not exhaustive, provide a solid foundation for selecting a venue booking software. As the process unfolds, it may feel like traversing a maze. But with the correct inquiries at hand, you'll be able to decipher the intricacies of the software options and choose the one that strikes the right chord for your event.