Do Dell and Fred hate each other or are they estranged?
Most likely. Although I like to believe that there was some affection between them merely because of this image
and Dell referring to Fred as "daddy" in the response "That's what my daddy taught me to do to backstabbers." But many parts of the game mean nothing or very little in the world of comic book canon. So a picture and a line don't really say anything.
Especially since Dell seems to have a closer relationship with his Grandfather, having significantly more photos of him and referring to him with much affection and respect in the canon.
Is Fred even really Dell's father?
Apparently, yes! I used to think not, and that there was room for other theories, like that he was Dell's uncle or just a distant relative.
This is never explicitly stated in the game or in the comics, but apparently the picture shown before has this name (this is on the official wiki);
Interestingly, this is literally the only explicit, canonical evidence that Dell is Fred's son
Did Fred know he would have to confront/kill his son if they fought the administrator?
Maybe yes, maybe not. We know that TFC started working for Gray Mann at the time all TF employees were laid off. So, if Fred and Dell communicated during that time, or by pure logic, Fred probably knew or thought that Dell was out of the loop on this whole thing.
probably reaffirmed by the fact that Dell didn't show up when they were going head to head with the rest of the TF2
They might have meet again in the hypothetical case that the TFC beats TF2 and they go to the coordinates indicated by Miss Pauling, but even then they couldn't kill Dell, because he would currently be the only one with the knowledge to make more immortality machines and better than the ones Gray Mann had
If Fred really worked for the Administrator, why doesn't he remember how to make or fix immortality machines?
Good question, there is no answer for that.
We already know that Fred is really Dell's father and that he really worked for TF. I would say it is an inconsistency in the canon. Anything beyond that is just speculation;
Maybe he forgot how to do it. From the time TFC was replaced until they reappeared, Fred was out of the picture for what seems like almost 10 years.
There's also the theory that he simply didn't want to help Heavy. Because his excuse was
"That damn thing's more biology than engineering..."
Like bruh... aren't you the same guy who made himself two fucking 100% functioning robotic legs + gave your best friend two fucking enhanced robotic eyes? You think I'm dumb or something?
Also, maybe it's just me who thinks that way, but that's the way he says it; "That damn thing's"
Honestly, I don't think any of the Conaghers really like immortality machines. Just based on what Dell tells us. Although all the Conaghers did not want to delve deeply into the administrator's plans, probably all of them (at least Dell did) were aware of what it was used for
They are aware of the cruel and terrible things that have been done to it and want to distance themselves as much as possible from it.
I mean, think about it. All the Conaghers had direct access to the plans for these machines, especially Radigan, who was the creator of these machines
And you tell me that NONE of them wanted to make one for themselves or for family or any loved ones?
If Fred was as scarred by this as Dell is, to the point of saying "if you find any more, get rid of it", it's understandable that he doesn't want to do anything even remotely similar for his friends.