Hebrews 11:8-9 (KJV)
8 By faith Abraham, when he was called to go out into a place which he should after receive for an inheritance, obeyed; and he went out, not knowing whither he went. 9 By faith he sojourned in the land of promise, as in a strange country, dwelling in tabernacles with Isaac and Jacob, the heirs with him of the same promise:
It could be contested that Heb 11:9 actually reads "as did Isaac and Jacob", as per the NIV, but that's not your question! In summary:
Abraham was 100 years old when Isaac was born (Genesis 21:5)
Abraham was 175 years old when he died (Genesis 25:7)
Isaac was 60 years old when Jacob was born (Genesis 25:26)
Therefore Jacob would have known Abraham for about the first fifteen years of his life. So yes, Abraham did meet Jacob.
Incidentally, there is an excellent tool I've recently discovered which helps represent information like this - The Amazing Bible Timeline.
I believe that the point of the verse is not to point out that Abraham lived together with Isaac and Jacob (although they did seem to do so at one point), but rather to remind the reader that all three generations lived as nomads in the land of promise during the course of their lives.
The word translated here as "tabernacle" is σκηνή - skēnē - which really means a "tent" or "temporary dwelling". It is the word, for example, in the Septuagint version of Adah bare Jabal: he was the father of such as dwell in tents (Genesis 4:20).
The point that the Church Fathers saw in this verse was that not only Abraham consented to live nomadically, but his progreny also. John Chrysostom comments:
And what marvel, if he himself [were so], when his seed also dwelt in this same way? For seeing the promise disproved (since He had said, “To thee will I give this land, and to thy seed” — Gen. 12:7; Gen. 13:15), he saw his son dwelling there; and again his grandson saw himself dwelling in a land not his own; yet was he nowise troubled.
