Principles
The reminders were revealed to humanity through the various messengers, but in all of them the target audience was humanity, not the messenger, whose job was only to deliver it (3:20, 5:92, 16:35, 16:82, 24:54, 29:18, 36:16-17, 64:12).
The Qur'an isn't for a few people to understand and disseminate to others - each person claiming to be Muslim has the responsibility to read and understand it for himself, because we are to uphold only what we know (17:36).
On God's part, He does not burden you beyond your capabilities for reading and understanding (2:286) and holds only you responsible for your understanding.
As a result, when we read the Qur'an we have to read it in a language that we understand, in the first person, and think - because God is addressing us, personally. The message isn't for the messenger.
It's inescapable that a word-for-word translation from any language to another doesn't lend itself to grammar and meaning, therefore all translations are best-efforts of the translator(s).
We must avoid a heavy-handed approach that imposes the translator's own understanding on the resultant text, especially if that understanding is derived from unverifiable secondary sources - like narrations, historical records, asbabul nuzul (circumstances of revelation, which are historical), and prior interpretations by others. These man-made documents should not be used to affect what we all consider as the absolute truth of revelation.
Furthermore, the Quran declares that God Himself explains it (75:19) from angles diverse angles for clear understanding. (17:41, 17:89, 18:54) and that God brings the best explanation (25:33).
So, read it without any preconceptions (rituals, rhetoric, concepts, philosophy?) (56:79) and silence your inner protests (7:204) from whatever knowledge you think you already have.
And hand yourself over to God for understanding, not any other human interpretation.
Therefore it stands to reason that the easiest translation to read would be one that uses the Qur'an's own definitions and explanations of the words and concepts it uses.
The Qur'an as It Explains Itself
In view of the above, my recommendation is to start with Dr Shabbir Ahmed's tasreef (an explanation from within the Qur'an itself). It's not a perfect translation or explanation, but it eschews man-made definitions and explanations for the most part.
You may start from here, at Dr Shabbir's Free Library Above all, think while reading.
Once you have the gist, idea, and sense of the general essence of the Qur'an, you may like to explore more traditional translations, such as Dr Safi Kaskas' "The Qur'an - A Contemporary Understanding" and make your own comparisons as to the differences. Dr Safi has revised his hadith acceptance criteria to be more in line with Quranic ideals.
Above all, think while reading.
Other Links
Deeper study for the interested
The Qur'anic Arabic Corpus (traditional word-for-word translations)
Lane's Lexicon (deeper dictionary of classical Arabic to English)
Lughat (Parvez's Quranic word dictionary)
Worldwide Quran Thinkers (redefining quranic words from within Qur'an)
Lamp of Islam (deep exploration of meaning of salat)
Hijra Calendrum (Deep investigation into dysfunctionality of the Hijra Calendar)
Newer Considerations
It will be inescapable for the reader to see that many words, even in Dr Shabbir's Tasreef, do not conform to traditional translations. Salat, for example, is not prayer - and linguistic studies give the meaning as communication, consistently throughout the Quranic text.
A more recent development reveals the meaning of two words - "rijal", traditionally translated as "men", and "nisa", traditionally translated as "women", to be the privileged part of society and the underprivileged part of society respectively. This revised understanding removes gender roles from many concepts and verses of the Qur'an, making it a more equitable and less misogynistic text (as traditionally translated)
Above all, think while reading. And good luck on your journey.
The Quran, for man, is in essence already known to him, rather than an entirely unknown entity. In reality, the Quran is the unfolding of the human mind. When one whose nature is alive—having saved himself from later conditioning—reads the Quran, those brain cells will be activated wherein God’s first address lies preserved. If we keep this in mind, it will not be difficult to appreciate that the translation of the Quran is a valid means of understanding it. - Wahiduddin Khan