TWA44

Hello, I am relatively new to Flyertalk and have only just started accumulating miles and points. I may not have enough for a September trip, and if I do not, I can buy tickets and use the miles/points for future travel. I am hoping that some of the veterans here can suggest the best ways to do the following:

Late August 2013 - Leave PDX (Portland, OR) for a city in eastern Europe or Turkey
Sept. 2 or 3 - arrive at TLV or ETH (the Eilat airport) in Israel
Around Sept. 23 - Fly from Israel back to PDX, possibly with a stop for a few days in ????

Rosh Hashanah starts on the evening of Sept. 4, and we want to arrive at Kibbutz Yahel around Sept. 3. The kibbutz is about 40 minutes north of Eilat and a few hours south of TLV.

I have flown to TLV many times but always directly from the states. I have never been to eastern Europe or Turkey. I will be traveling with my husband.

Starting in late November, my husband and I opened accts to get bonuses from US Airways MC Barclays, Hilton Amex, Chase Sapphire Preferred, Hilton Citi, AA Citi, and Club Carlson. I opened a US Airways MC Barclays. Once we finish our latest round of minimum spends (late April/early May) I will open a few more cards in my name. Here are our current miles/points balances, meager as they are:

Me:
AA 28,378
US 40,072 (plus 15,000 after completing extra spend to get more points)
Under 10,000 each in SW, Delta, UA

Husband:
Delta 48,914
AA 14,292 (plus 30,000 after completing spend for new card)
US 40,241
Hilton 88,596 (plus 50,000 after finishing spend for new card)
Points on old cc: 30,045
Chase Sapphire 48,000
Club Carlson (will have 85,000 plus points soon)

While I hope that as I acquire more and more points that I can in the future travel Business class, I am fine to go coach this time. I am also OK to pay for well priced tickets rather than scramble to acquire enough points in time. My thought given the balances I have is to probably pay for flights and use points for some of the hotels, but I'd love your expert advice on:

1) a good city to stop for 4-6 days before going to Israel
2) best way to get from PDX to that city
3) best way to get from that city to TLV or Eilat airport ETH
4) best way to get home directly from Israel or with a stop in ????
5) best cards to consider for me to apply for in April/May (I am thinking the AMEX AA for 50,000; the Chase Sapphire Preferred for 40,000 and a hotel card or two, depending on minimum spends)

While we do not have much flexibility re: arrival date on the kibbutz - Sept. 3 is best, Sept 2 next and early on Sept. 4 do-able only if necessary - we do have flexibility on the date we'll leave PDX (August 25 or 26, plus or minus a day or so on either side) and the date we'll come home (Sept. 23 plus or minus a day or so on either side).

A friend who is a few months ahead of me in the points/miles game suggested booking roundtrip tickets to eastern Europe or Turkey, and then finding a charter/cheap flight from there to Israel. Is there another better/cheaper way to do this trip?

Thanks so much for any advice/help you can offer!