January Deadline w/ low GMAT vs. Final round w/ better GMAT score?

The schools I'm interested in applying to have a middle 80% GMAT in the range of 620-690. With 2.5 weeks remaining before I take the exam, I have not yet reached those numbers.
Currently, about 3 weeks into studying I'm still around the 550 mark, which is only an increase of 40 points over my "cold" score. I plan on sticking with my exam date in two weeks, but plan on taking the test again mid-February (@6 weeks later).

My current plan is to study about 3-4 hours, daily, until my test date. And, maintain a 2-3 hours a day routine through my second exam date. The goal of my first exam is to get a feel for the GMAT, post a score, then use that info to attack date #2. If, by chance, there's a dramatic increase into the 600s over the next two weeks, I will submit those scores (I realize that's a low % proposition currently). My ultimate goal is a 650-680, so i'm 100+ points from that goal with about 8 weeks remaining.

I'm coming up on the "guaranteed consideration for funding" deadlines for most schools in January. Should I submit my application with B+ recs, A- resume, A+ community service, low GPA and low GMAT (assuming a 550-580 or so) RIGHT NOW to meet the funding deadlines? Or, miss this round of deadlines and apply during the final round (which I heard is the worst round to apply) with a bit better candidacy (assuming mid 600s GMAT)?

Is there a study schedule out there that you would recommend, or should I craft my own? I thought of the 3 month Magoosh plan as a base, but didn't see much recent feedback. I had followed their 30 day play through the first 8 days, before coming across the Manhattan guides.

My current study materials are Kaplan, Magoosh, and I just purchased Manhattan Study guides and Interact (sweet deal on eBay last week). The Manhattan guides rock and will be the focal point going forward, they've really helped my brain digest the information.

Thoughts, comments and/or suggestions?

Kaplan 500 38Q, 19V (Cold mid November)
Manhatt 530 37, 26 (12/12)
Kaplan 540 36Q, 27V (12/16 Pearson test Center)