Answering question by question in bold:
Quoting Cop Luv >>> Just seeing if the new CSR is for me and need some advice:
1. I have never had a card with an annual fee on it, so choosing one so large is a hard pill to swallow.
Keeping it after a year may not be the right thing. If you get it and are able to use the travel statement credit before this year is out and before your annual fee is due next year that alone will have given you $600 if value which more than covers the annual fee. Add in the 100,000 UR points and there is another $1500+ in value. I will pay $450 to anyone who will give me back $2100 in return 
>>> 2. We travel MAYBE once a year to Florida (not Disney) and stay in a family condo, so the only "travel" expenses would be a rental car and airfare.
3. Is the CSR the best for travel perks only?
In my opinion yes, but I imagine there are others who might disagree. Now I am speaking long term value not the awesomeness of the bonus for the card right now and the first year. There are plenty of great no fee cash back cards and strategies to use them for those who don't travel much.
>>> I have had a Freedom card for a number of years as my primary card. If I were to transfer UR points from the Freedom to CSR, then they would be worth 1.5x more?
No they would be worth 1.5
>>> Would they only be worth the 1.5x if you were to use them booking travel through the Chase Portal?
Yes. Is that the best use of UR points now?
Not in my opinion but I value airline miles more than using my points as a cash.
>>> I was reading The Points Guy and a lot of their articles are outdated and don't include the CSR in their "best use of points" analysis, so I wanted to make sure I had the most up-to-date info, and am doing the math correctly.
The card was just released on August 21st.
>>> I checked airfare to FL for a possible trip and the Chase Portal had it for $230. Kayak had it for $207. United Mileage points had it for 12,500 points (saver).
Make sure to check if that was just one way or round trip. United will show miles required each way.
>>> I have roughly 12,500 points in UR with my Freedom which would transfer at 1.5x to 18,750 on CSR????
No. It would transfer to 12,500 UR points that can now be used to book travel or directly transfer to an airline.
>>> I can purchase one ticket with a 1:1 transfer to United Mileage through CSR, correct?
You can transfer UR points directly to United from a CSR, CSP or Ink+ at a rate of 1:1 and turn them into frequent flier miles. Then you can redeem an award ticket on United.
>>> Or I can purchase one ticket for $184 through the Chase Portal with the 20% CSR discount as long as I use my card (and get travel credit), correct?
Yes, you would get the travel credit, for paying with the card. The 20% discount when redeeming points for travel.
Or Can I purchase the ticket through Chase Portal using points?
Yes. Would it be 23,000 points (original price) or 18,400 points (20% off price) to which I would have enough of?
If you get the CSR and make the required bonus spend you will have over 100,000 UR points. 100,000 UR points on the CSR is worth $1500 in the UR portal.
>>>Or I can purchase it through whichever website had it for $207 (this would get travel credit).
Yes.
Am I thinking too much of this? I just don't need another card if it is going to end up costing so much with the Annual Fee. Thanks!!!
If you can make the bonus spend and utilize the $300 credit both this year and next year then definitely get the card. When the annual fee comes due next year you can downgrade the card to a CSP or Freedom Unlimited. The break even point for keeping this card over the CSR is if you spend $3200 a year in dining and travel. I hope this helps.
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