1. If you can meet the MSR on a CIP#2 without throwing off your plans too much, definitely go for it because, like I said, a loophole like this will be closed sooner than later. Remember, keep it simple. FirstName LastName, sole proprietorship, SSN as TIDN (and since you have your own business, I'd also add that I've noticed high/six-figure+ revenue seems to trip additional underwriting and documentation.)
2. CIP#2, being a Chase card, will not throw off any of your plans with Amex, i.e. their Bonvoy cards.
3. However, note that the Bonvoy Brilliant (I'm assuming that's the personal card you're referencing) 100k Marriott points offer ends on 4/24/19.
4. As you're aware, Amex has a 2/90 rule that will deny a new card application if you've already been approved for 2 Amex (personal or business) cards in the last 90 days.
5. You were approved for the Bonvoy Biz on 3/20/19, and it looks like you were approved for the Hilton Biz on 1/27/19. 91 days from 1/27/19 is 4/28/19, which puts you past the end date of the Bonvoy Brilliant's 100k points offer.
6. However, as you know, you can apply for a card before the end of your 90 days purgatory, get "pending review" or denied for too many cards within a certain period of time (2/90), then recon after the 90 days are up (like you did with the Bonvoy Biz). So, even though you are 2/90 with Amex until 4/28/19, you can apply for the Bonvoy Brilliant before the 100k offer ends on 4/24/19 (don't wait until the last minute/day), let your application go pending review, then a few days later -- after 4/28/19, call Amex to recon the app. Since you timely applied under the 100k offer, that offer is still attached to your app even though it's approved after the end date.
7. One last thing, note that Amex has a 5 Amex (personal and business) credit card limit. It looks like you've already got 3 (the Hilton Aspire, Hilton Biz, Bonvoy Biz), and the Bonvoy Brilliant would make 4 (unless I'm miscounting). Once you hold 5 open Amex credit cards, any more apps for Amex credit cards will also result in pending review/denied unless you can close one of them. DO NOT close any Amex card that's been open for less than a year. It's in the terms that you agree to keep them open for 12 months, and closing an Amex card within a year will result in clawback of the bonus and/or the pop up based on your history. Note that Amex charge cards (the Green, Gold, and Platinums, and their business varieties) don't count against the 5 Amex credit card limit.
Hope this helps give you a clearer roadmap.