These are just a few of the high level questions. Do I want to spend a reasonable amount of money on software or use a free one?.
Do I want the logger to accept QSO logs entries from other applications such as WSJT-X and others?. Do I want the logger to send logs to LOTW, eQSL and others?. Do I want a logger to run on Windows, Linux or Mac?. application and database can be moved between devices)? Do I want a logger that is portable (e.g. Do I want just a simple logger (no callsign look up)?. Do I want software that is good for general logging as well as contests?. Do I want software that will help me chase awards? or generally logging?. You are being asked, in the very early stages of your hobby to select and invest some time into your logging software, and to take a guess on how you want to use and what features you need in your logging software. Strangely enough, besides the purchase of your radio(s), this is one of the hardest decisions to make. 
Very simple answer to this question, and it may sound like a “duck and a swerve”, but the best logging software is the one that suits you, the services you use, the requirements you have and how you use amateur radio.
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