After sitting back and watching all the fun you all have been having because I was in the process of relocating (selling one house and buying another) I am so ready to get going

. We finally closed yesterday, I used Chase for the new mtg. I will be converting a free-standing building to a pool/guest house so will have lots of opportunity to spend. I am 1/24 (CSR 9/16). I usually fly SW out of Midway, and United out of ORD (Chicago). I have a small side business which I think will qualify my for business cards also. I have two points goals,
- Take my family of 7 plus two infants to WDW in Dec on SW. I know most want to open 2 SW cards for the companion benefit. I want to open 2 to use the points for this trip. It will take about 130k points.
- Take my family (which will be 9 by then) to Aulani in 1/2019 on United (the only NS out of Chicago). I have not seen that many seats available the few times I checked the rewards site so I know this may not be an option for the entire group.
I think I need to apply for both SW cards asap (preferably on the same day) one business and one personal. That will put me at 2/90
I am confused about what order to go in after that. Will I be at 3/24 or 2/24? Does business accounts count against the 5/24 rule? If not I would wait the 90 days and then go with a personal and business United (again applying on the same day).
I have received offers from Citi AAvantage 60k points and Discover it with matching cashback for 1 year. I would like to get those too but I think they could interfere with the SW & United plans above or future Chase options.
I appreciate you insight and suggestions!
Thanks