When you enter the land that G-d, your G-d, is giving you as an inheritance, you must take possession of it and settle in it.
When you enter the land: The word for "land" in Hebrew (eretz) is related etymologically to the word for "will" (ratzon). Based on this, the Baal Shem Tov expounded this verse as follows:
When you enter the land: When you succeed in aligning your will with G-d's will--
That G-d is giving you for an inheritance: this ability being a Divine gift innate to you Divine soul--
You must take possession of it: your challenge is to integrate this newfound will into your daily life, so that rather than divorcing you from reality, it enables you to work within reality in order to rectify it.
Take...the...fruit...and place it in a basket: In order to properly rectify reality, ensure that your heightened consciousness (the "fruit") is vested in the appropriate means of expression (a "basket").
Go to the place that G-d, your G-d, will choose: In the context of working to rectify reality, be aware that when you travel from place to place, you are not doing so on your own; rather, Divine providence is arranging your movements in order that you disseminate Divine consciousness wherever Divine providence leads you.
Later, the Baal Shem Tov expanded on this idea, uncovering an additional layer of meaning in this verse:
When you enter the land: In order to align your will with G-d's will--
Go to the place on which G-d, your G-d, will choose to rest his name: Devote yourself selflessly to disseminating Divine awareness wherever you are. And how is this done? By even the simplest of means, such as reciting a blessing over food or reciting a verse from Psalms.
In other words, we should not allow our intellects to convince us that we are incapable of influencing our environment. The fact that we are where we are indicates that G-d has both placed us there and has given us the spiritual wherewithal to disseminate Divine awareness.
Furthermore, fulfilling our Divine mission in consort with G-d's providential cues will bring us material blessings as well: Divine providence works in the guise of natural cause-and-effect to bring us where we are (we thought we there for the sake of some material need), so fulfilling the spiritual purpose of our being there will bring G-d's beneficence into the natural process that worked to bring us there.
Moreover, if we integrate our Divine inspiration into our daily lives, remaining constantly aware that our footsteps are guided by G-d, then we will ipso facto disseminate Divine awareness wherever we go.
Allegorically, the notion of "entering the land" alludes to the descent of the soul into the body. This descent is quite drastic in that the soul forsakes its spiritual abode only to find itself challenged by a physicality so overwhelming that it totally obscures Divinity. Yet, this descent is still, ultimately, a joyous event, a veritable gift "that G-d, your G-d, is giving you," because the soul before its descent into the body can only experience the grade of Divine consciousness endemic to its "location" on the rung of spirituality. But in the course of fulfilling its mission in the physical world, it acquires the ability to experience much higher levels of Divine consciousness. Thus, its descent into this world results in an ascent after it leaves the world to a level higher of Divine revelation than it had ever known.