Can you help me understand points and transferring points?

I feel so dumb for asking because I’ve watched videos and read articles and posts, yet I’m still confused. I’ve never had a point card before and it’s overwhelming. CSP btw.

So I know I can transfer to United for example. I was having a hard time knowing when it’s worth it until I saw a video that said on United’s site you can view by point price. It said you take the total cash price less the fee and divide it by the points price to get the price per point. I’m guessing that’s to see if it’s better than chase portal? Better than the typical 1.5 cent value?

Anyway a few other things confused me.

1. For some reason United wouldn’t let me select a return flight. It showed me the departure flight for 70K points. But then it kept saying no flights available during my dates to select a return flight.

2. On United when I search it’s in miles and their mileage plus program. When I ask chase to transfer to United do the chase points convert to those miles? So I can assume 1 chase point equals 1 mile award?

The other thing I’m confused about is Hyatt. I’m searching by points and as an example a room is 18,000 points per night. Does that mean I would transfer 18,000 chase points? How do you determine if it’s cheaper to transfer, do chase portal, or cash price?

Sorry I feel dumb for being confused but I’m having a hard time understanding how it works. I don’t mind taking the time to research and work for a good price but idk how everyone else does it.