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your uncle can't/won't come to the wedding presumably because he has to fly in a day early, which is yom kippur? and he won't fly in earlier than that because...? this sounds like a problem with him, not the date. many people i know go to a different shul on the high holidays because they're traveling to celebrate with family, so it's not like it's unheard of to go to another shul. however, i am definitely not a definitive source on all things jewish (and definitely not on orthodox judaism or on how the high holidays are celebrated in israel).
that being said, i originally thought that the period in between rosh hashanah and yom kippur was off limits for weddings (according to my mom, who sometimes makes this stuff up, so you probably want to double check that), so that time might not be that much better for him.
i'm assuming that sundays in early september or november aren't available? if his presence there means a lot to you and he would otherwise come if it wasn't the high holidays, i would change the date. but i would try to first fully understand his concerns before you switch it.
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I think the 12th would be the best in terms of Holidays, the 5th could make it more difficult for some and like you said awkward. If there is anyway you could push it to November (but for relatives from Israel -November is the start of Israel's 60th celebration) that might be better? If not, stick with the 12th, find your uncle the orthodox shul. You might have to make a sacrifice here, no Uncle, but your mom & grandmother. Good luck!
I would do it sooner and skip the details/DIY stuff and delegate, delegate, delegate. That way you can have the people you care about there which is really the important thing.
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Rebecca,
Since Yom Kippur falls on a Thursday this year, and he cannot fly on Shabbat, he would have to observe Yom Kippur here in the States. I just wrote his daughter and asked if she would talk to him and see if he would be willing to go to an Orthodox synagogue here. I will do whatever I can to respect his level of observance, even find him a nearby room so he can walk to synagogue (he does not get in a car on Yom Kippur).
ahhhh, i see. in that case, i think you're doing all that you can to make sure that he's taken care of. i think you just have to sit down with your FI and weigh the pros and cons of moving the date. good luck!
Given your personal situation, I say pick the date that works best for you and try to accomodate people like your uncle. You won't be able to pick a date that works for everyone. That said, if you have a lot of Jewish guests, any weekend near the holidays will be challenging if they need to travel for your wedding. I like the idea of moving it up if possible to September- might be worth it!
Why can't you use the 19th? I am getting married on the 19th and it's a Jewish Ceremony with a Rabbi.
Hi, Debyeb27. The rabbi I checked with told me it's not a good date on the Jewish calendar and to be honest, I have tried to understand the significance of each date but I don't really remember why. Are you getting married in 2009? Because we were only talking about 2008.
If that's your date, mazel tov and enjoy your day! I think things like this only matter to people who care about them, but the ultimate mitzvah is getting married! If your rabbi didn't say anything about the date, I wouldn't worry about it.
Maybe I will check again with another rabbi about the 19th. :)
We're having our Jewish wedding on October 12th also. I am worried that some Orthodox family will not come because of travel difficulty, but I will offer to accomodate as much as possible.
You are typically not supposed to have weddings during Sukkot (the 19th) and while Reform rabbis may perform the ceremony, your Orthodox uncle likely would not attend then anyway. Having the wedding between Rosh Hashanah and Yom Kippur though technically allowed probably still makes it difficult for him to travel with the various holy days in between the two holidays.
I say if you're happy with the date, go with it. Give your uncle information about a local Orthodox shul and home hospitality options within walking distance. Hopefully he will come, but if not, just realize that whatever date you choose will inevitably be impossible for someone and what's most important is something that works for you and your fiance.
Hi, EK. I just looked up a list of Orthodox shuls in the area, spoke to my dad, and he agreed that he will stay the night at a nearby place and go to shul with his brother in the morning so he won't be alone. He's going to talk to him about it tonight. I am hoping this means the problem has been solved!
Thank you for explaining the issues with the dates surrounding the High Holidays and Sukkot. :)
THANK YOU everyone for all of your helpful opinions! 
I really appreciate all your input.
~Akimbo
I feel for you--I'm Jewish and getting married this fall as well. We opted to go before Rosh Hashanah this year though because I didn't want to get married in November! ;) I totally understand the predicament...
It does seem a bit weird to have the wedding after R"H but before Y"K, even if it is technically allowed. When we discussed dates with our rabbi, some dates that seem "clear" for us would not be for him because the holidays are the biggest and busiest time of year for the rabbi too.
I guess you would have to think about how important it is to have your family from Israel there. Is there any way a date in Sept would work for you?
B'Shaah Tova!
I'm glad it's looking up for you. Just wanted to say I feel your frustration! We were thisclose to booking a reception site on Oct. 18 because our Reform rabbi said he had no problem performing our Reform service then, even though it's during Sukkot. We double-checked with my FI's Chabad rabbi, though, and he let us know it was absolutely forbidden. So, we pushed it to Oct. 25 and had to find a new venue. Now, to figure out how to bring in a handful of kosher meals...
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I don't know how many here are familiar with Jewish wedding dates but there are certain days in the year that traditionally, one should not get married, and certain days that are auspicious. After checking with a few rabbis, we have pretty much decided to get married on 10/12/2008, the Sunday after Yom Kippur.
I was hoping that my relatives from Israel would fly to California to spend the High Holiday with us but my uncle is very religious and now says that he might not be able to come to the wedding. I am happy to find him an Orthodox shul and room withing walking distance. Now my father is upset and wants us to change our wedding date, just as we are about to sign the contract with the venue!!
Am I being unreasonable or should I try to have my wedding on October 5 instead? That's during the Days of Repentance between Rosh HaShanah and Yom Kippur so it's awkward (for us and many guests who might have wanted to make a vacation out of their trip). The venue is booked on October 26, and the 19th is prohibited.
I do not want to push my wedding date further back because my mom and grandmother have been very ill for a while. I do not know if I can get everything together if we do it sooner, however. Please advise! What are you opinions? What would you do?