Wow, thanks for all the information. This is a great resource. Here is a quick rundown of my situation:
I've had the Chase SWA Plus Business card for nearly a decade and have earned a companion pass with my spending for the last 6 or so years. This has been my "primary" card and I used to put pretty much everything on it (to make sure I got to the companion bonus).
I also have carried what is now the Hilton Ascend card for about 7 years and used it when staying at Hilton properties and when I met my Companion Pass threshold each year.
The card I recently got is the Chase Sapphire Preferred (sorry for the confusion), but Thunder was very clear when that card should be used. Since I got it, I have put every single meal I've eaten on it (including fast food) and will continue to do so.
I think I'm up to 2/24 at the moment. Between the CSP and the fact that I applied for a chase card for one of my business entities and due to a technicality (they didn't like that the mailing address and physical address were different), I never finished that application, but I know they ran my credit so I assume that counts toward my 5/24. That leaves me 3/24. Also, I didn't think about doing my wife's cards separate, so I will do that from now on. I did the CSP as a join application, but will make sure to use her remaining 4/24 wisely.
Lastly, on the travel, the goal is to get Business or First class going East and Business/Premium Economy coming West, being what every I can afford.
Follow up questions:
Can I get multiple small business cards? I have a couple more business entities that don't have case cards attached to them, so could I get multiple 80k bonuses?
Since my wife it co-owner of several of the business entities, do you guys know if they will flag it if I have her separately apply for a business card for the same entities for which I have a business card?