In your quest for the most suitable plant breeding software, a series of well-structured and insightful interrogatories to potential software providers is paramount. This engagement is not unlike Socrates’ elenctic method, where through a process of questioning, one could expose the contradictions in someone's beliefs and, in turn, lead to the discovery of universal truths. A deep dive into the who, what, when, where, how, and especially why of the situation is expected.

To commence with, it is essential to understand the pedigree, the "who" behind the software. Is the provider well-versed in both plant breeding and software design principles? Just as a plant breeder would expect to know the lineage of a potential plant cultivar, the pedigree of a software provider is equally essential. This is reminiscent of the discourse on pedigree seen in the works by Richard Dawkins in the field of evolutionary biology. His concept of "the selfish gene" elucidates the idea that genes, not organisms, are the principal unit of selection. Similarly, it's the underlying pedigree or collective expertise of a software company, not just the superficial brand name, that plays the key role in shaping the quality and suitability of a software solution.

Next, elucidate the "what," the core features of the software. Query about the primary functions, such as data management, statistical analysis, and predictive modeling. However, remember the Heisenberg Uncertainty Principle from quantum mechanics that posits that the position and the velocity of an object cannot both be measured exactly, at the same time. In a similar vein, be aware that software that excels in all areas may be as elusive as measuring the position and velocity of a subatomic particle. Prioritize features that align with your specific needs.

The "where" and "when" aspects concern the accessibility and updates of the software. Is the software cloud-based, or does it require a specific hardware set-up? How often is the software updated? Can it seamlessly integrate with your existing technological infrastructure? This is not unlike the compatibility of gene sequences in plant hybridization processes, where the compatibility between different plant species plays a crucial role in successful cross-breeding.

The "how" is about the interface and user experience. Here, the concept of ergonomics, a scientific discipline concerned with the understanding of interactions among humans and other elements of a system, is important. A software with a sophisticated algorithm but a complex interface would be like a plant with excellent genetic potential but poor survivability in a given environment.

Lastly, and perhaps most crucially, comes the "why". Channel your inner Nietzsche and dig deeper into the raison d'être of the software. What problem is the software designed to solve? How does it plan to make your work as a plant breeder easier, more effective, or more innovative? This touches upon the principles of utility from the realm of economics, where the usefulness or satisfaction derived from a good or service greatly affects its value.

Remember, the perfect software doesn't exist, much like the perfect plant. Both are dependent on their environment and the specific needs they are expected to satisfy. Much like the process of Mendelian inheritance where the traits of an organism are determined by the combination of genes it receives from its parents, the right software will be one that best combines the desired features to suit your unique needs.

In conclusion, asking the right questions to your potential plant breeding software provider is an exercise that demands depth, breadth, and agility in thought, much like navigating through a Harvard curriculum. It requires you to be a philosopher, a scientist, an economist, and a mathematician, all at once. Only then can you find a software solution that truly resonates with your unique needs, and empowers your work in the endlessly fascinating field of plant breeding.