Contextualizing…

I have been thinking... Up to what point can one contextualise the gospel? Before i answer the question lets define “contextualising the gospel” and give an example or two.
Urban dictionary gives this definition of the word context:

The circumstances or events that come before and after a particular word or passage in a speech or piece of writing which helps explain its full meaning.
For example
Context: You are playfully poking me in the side
"I'll kill you if you don't stop!"

Contextualising is when the meaning of anything, be it actions, words pictures etc. are put into a context that makes sense to a recipient and helps them understand the intended meaning.
I found some really interesting info on the Mediterranean culture of Paul's time, relating to gifts.

..in Rom 15:27 Paul calls the “freewill” offering made by the churches of Macedonia and Achaia for the Jerusalem saints a “duty”. This, on the surface, would appear to a         modern non-Mediterranean reader to be a conflicting statement; since, in many modern cultures, a strict distinction is made between a freewill gift and a duty. In Paul’s Mediterranean culture however, there was no such thing as a completely free gift. The reception of the gift placed the recipient under a certain reciprocal obligation, at least to acknowledge the debt of gratitude...Reciprocity was one important cultural value that bonded the Mediterranean societies together. Annang Asumang (2009:8)

I find it fascinating how this would have affected their view on the free gift of Grace we receive. These people would most likely have automatically realised that: yes, we got a free gift, but that accepting it placed them under a huge obligation towards God, to the extent that he actually owns us and we owe our lives totally to him. What's even more interesting to me is the similar Maale culture (in remote Ethiopia) of giving gifts and the reciprocation thereof. The tradition, as far as i remember, went along the lines of someone giving me around 3 gifts and me reciprocating with a big gift (vice versa), thus sealing our friendship forever.
Perhaps this is a good example of how contextualising the gospel can work, if parts of the culture benefit the persons understanding of God's word and salvation, great, so long as it doesn't change or replace the gospel in any way.

I think a good Biblical example of contextualising is in Acts 17:22-23,

Paul then stood up in the meeting of the Areopagus and said: "Men of Athens! I see that in every way you are very religious. For as I walked around and looked carefully at your objects of worship, I even found an altar with this inscription: TO AN UNKNOWN GOD. Now what you worship as something unknown I am going to proclaim to you.

Its interesting that Paul didn't barge in and rebuke the "gods" of these well learned people, but rather used their beliefs to introduce the gospel.
Other verses that come to mind are: 1 Cor 9:19-23 "...I have become all things to all men so that by all possible means I might save some..." (e.g. Adapting to the culture) and Rom 12:17-18 "...Be careful to do what is right in the eyes of everybody.." (e.g. dressing appropriately).
With this in mind it is vital that ones identity is found in Christ and not any culture. I think culture is great to the point where it helps us to relate to God on human terms, in our understanding, but it is an aid in pointing us towards an understanding of God, not a tool with which to box God into. Therefore every culture has something very valuable to 'reveal' about God (since mankind is made in His image), but the culture is not the point, God is. What do you think?