I think we will need to clarify few things first. Only then we can attend to the easiest way.
What do we mean by most similar remedy?
On what level?
I know one source that can give the fullest information that can lead us to the most similar..
and that is.... patient himself!
Hahnemann says we need to be unprejudiced observer to faithfully sketch morbid totality.
And, then he also says we need to be understanding of human psychology, circumspect, deliberate, tactful and with profound patience.
So, finding the similimus is about case taking and analysis and knowledge of materia medica!
Analysis and repertory and materia medica can be computerized.. but case taking is the human art and the most critical part of the whole exercise.
My gut sense says that to answer your question we will need to address this part!!
But, do you think it right to put the cart before the horse?
I think that tact and technique is secondary. First and foremost, it is doctor's attitude that permits the patient to be himself and trusting. Only then, he feels comfortable in sharing what he holds back due to several social fears and inhibitions.
And, the right attitude can also facilitate the patient to access even that information which was unconscious in patient till now. Such a case taking not only helps us in reaching to a "deeper similimum", IT is therepeutic in its own right.
IT demands few things from us. One, to be our genuine human self. Two, to be really and non-judgmentally interested in the human being in front of us. Three, to understand our patient from his point of view.
It is an experiential shift. Just conceptual knowledge is not enough. I find that I can not take this attitude for granted. In fact, every opportunity is a fresh challenge.
Sameer, I know this is not a "to the point" response to your pointed question. But, I would love to engage more fully in exploring if you feel interested to find out what all is implied in this.
In Homeopathy we frame the totality of symptoms by treating the individual as a whole .We do not treat any particular organ or system but the individual as a whole by proper case taking ,finding the similimum with the help of materia medica and repertory.By practice and experience and deep study we can easily do it but hard work and dedication is required