1a. Is that 81k all on Chase cards? It sounds like not. Chase is looking at the amount of credit they have extended you when they make risk determinations, not the credit you have with other issuers. So add up all the credit from Chase cards and then look at the ratio of CL to income. Some other folks can chime in with recommendations but what I have stuck in my head is be less than 50% CL to income when applying. I think some recommendations are around 30%. Also what they have already extended you may be a good indication of what they are comfortable with.
In addition to that, Chase won't move credit from a personal card to a business card. So if you were going to apply for the CIP again you'd have to reduce your CL's in advance. If skipping it and just moving on to personal cards you could maybe offer to move credit around if denied so you may not need to preemptively reduce CL's.
1b.
Don't close anything! 
As a few others have mentioned already, just ask to have your CL lowered. You can do it through the Chase Secure Message feature if you don't want to call. I did that the other month and they were super responsive (most were completed same day).
2. A. If you only get to 4/24 and get approved for the CSR then you're at 5/24 and won't be able to get the CF or CFU until something is removed. Also, Chase has a 2/30 rule for personal card applications. So you should be ok with one card but need to wait until 30 days after the CIP application for another card.
If you wait until 30 days after (really, 31
) then you could double dip the CSR and CF/CFU on the same day. But that still puts you at or over 5/24 and you'd be shut out from the CIP if you were really interested in it.
2. B. That's an interesting thought there with the double dip of CSR/CIP. That'd put you at 9k in spend within 3 months; without the DVC rental is that doable? If you attempt it, you'd have to do the CIP first as business cards have a 1/30 rule.
I almost feel bad...
