2 Questions That I'm Probably Overanalyzing

I have a habit of overthinking - and I honestly feel that in my elo, my overthinking is what's killing me.

There's a dude that's just running in with a judge, thru a Brim caterpillar smoke and HE LOOKS LIKE HE'S HAVING MORE FUN IM NGL

But with that being said, I had just 2 questions w/ "scenarios" that I would love your input on.

Question 1

When I plant the spike, my first instinct is "the wincon is (A) spike time and (B) numbers advantage. But since I solo queue often, I find that there's many instances

where a dude will just "run off" on their own (i.e. to CT) to try and continue fragging.

Though I comm as much as I can - there's just too many cases of this occuring.

In this instance - even though I know that the wincon is first to the spike, is it wiser to chase after the guy and potentially refrag? Or, is it right for me to anchor / protect the spike to detonation?

Question 2

Let's say that we lose pistol round. My instinct is to save - but 2/5 teammates force up a stinger or something else).

Is it better to "force up" together, or stick to the eco route?

Sorry if these questions are silly. I'm deep in Gold/Plat and everyone has differing opinions.