Hi guys,

I'm fairly new to points and miles and this is my first post on FlyerTalk. (Note: If this isn't the right thread, sorry about that! -- mod please move it to correct one).

I've spent the past month absorbing all of the Boarding Area blogs to learn what I need to do, and signing up for all miles/points accounts to prepare.

Kinda long post.. so I put a TL;DR at the bottom.

Here's My Predicament :

I really, really want to take my wife on an awesome vacation to Hawaii for our 2 year anniversary in February.
(we couldn't really afford anything for year 1, and honeymoon was kind of a bust as well :-\ )

I've already got a head start, but don't have much time left to acquire points and want to know the best way to do it. (and avoid any useless CC sign ups!)

Some Background Information

- [Edit] My wife cannot get any CC's because she just became a greencard holder and doesn't have a credit history in the US. We're starting her off with Student CC to build credit.
- [Edit] CVG is home airport
- [Edit] Spending capacity is about $2-3K per month
- I currently have 78,000 Delta SkyMiles
- I need 130,000 miles + $20 to go coach from CVG to HNL from Feb 22, 2013 to Mar 3, 2013 (doesn't seem so bad! Don't think I could swing First class though)
- I've had the Delta SkyMiles AMEX Gold card for 3 years now
- I have no other points anywhere
- I have 2 other crappy CC's that carry a balance and do nothing else for me
- My FICO TU score is 710 (as of 8/1/12)
- My FICO Equifax score is 670 (as of 8/1/12)
- I'm concerned about the difference in scores
- I've been paying down CC debt significantly over the past 2-3 months

My Goal

- Fly us both RT CVG to HNL for $20 + miles
- Stay at least 6 nights in SPG hotel level 5 or up (using cash + points if necessary)
- Stay another 4 nights somewhere cheap (~$100/night?) if necessary due to not having any more points for nice stuff

My "Noobie" Plan

- Get the Personal AMEX Platinum Delta SM card with 30,000 miles
- Get the Business AMEX Platinum Delta SM card with 30,000 miles

- Get the Personal AMEX SPG card with 10,000 points (plus 15K points after $5k spend in 6 months) probably doable
- Get the Business AMEX SPG card with 10,000 points (probably can't make second spend req.)

Total SM : 60K new SM + my current 78K miles = 138,000 (enough for trip)
Total SPG : 35K SPG points (enough for 7 nights + $90 per night at Level 5 Westin Waikiki)

Major Questions

- Can I actually get that many AMEX cards? or will I likely face a lot of rejection
- Are there any other ways to get good Delta SM outside of AMEX?
- I do actually own a business. Can I get both personal and biz AMEX cards on same app o rama?
- Am I missing any big promotions, problems or pitfalls?
- Should I aim for 1 big card application day, or try to get 2 in? (I have roughly 7 months until the trip as of TODAY 8/1/12)
- Do I receive the points in my account within days/weeks of getting approved?

I'm not "married" to this plan at all, I just want to take my wife to Hawaii for 10 days for very cheap! And this is all I could think of.

Please advise if there are any other ways that would work out much better.

Thanks SO much,

Jordan

TL;DR - I'm a travel hacking noobie who really wants to take his wife on our first amazing trip. I already have some Delta SkyMiles. Please help!