If I wanted to make a Pleasantview of the past, how would I go about doing it? When I say 'of the past' I mean Mortimer and Bella with child Cassandra, Brandi married to Skip Broke with baby Dirk (with her parents Bob and Betty alive), and so and so? I know it would involve SimPE, which I know how to use a bit, but what would I have to do? I don't want to make an entirely new neighborhood with new characters as they wouldn't have their memories and family trees.

Not sure about Brandi being married to Skip since as I understand it he doesn't actually exist past being part of the story and stuff so I don't think you could bring him back to life, but the rest of them you can bring back to life (though I thought Bob and Betty were still alive) and age down the Goths, though I dunno what you'd do with Alexander unless you aged him down to baby or something.

That's just what I'd do

Granted I'd be doing this with inSim, not SimPE, so I can't help with that part.

So do you mean this to be a alternate history of Pleasantview past or am I just being a mite thick here? I'm guessing you got Dustin and Dirk mixed up seeing as Dustin is Brandi's son. But seeing that he and Dirk are kinda portrayed as brothers by different mothers I can see how the inversion would happen. You have Brandi with Skip so I would think you intend to do it straight. But then again. . .

I looked into it a bit further and saw that memories would have to be altered for it to make sense so I might not do it anymore :/ Too much work and I don't feel like doing it.
I might make a TS1 neighborhood instead.

You could just start from scratch; either download the ones you need from somewhere like the Exchange or just extract them from SimPE and start the families over again. You could edit their family and friendship levels again in SimPE and go from there.

The Aussie Topenders people made really good Bob and Betty sims, if you're interested: http://www.aussietopenders-sims2.co...AndGenetics.htm

This site might help too: http://simestates2.planetthesims.gamespy.com/

Skip exists, he's in the family tree and memories, it's just that his grave is gone (deleted?)

There wasnt a grave(I think...) If the sim drowns then where is their grave underwater, not quite sure.

... no it appear next to the pool

http://www.genensims2.com/guest/Mad...bourhoodsS1.htm has all, if not most, Sims 1 families + houses for download.

Actually, TSR (of all places!) has the original Sims 2 families for download-they're free, too. Look under the "Family" downloads and you will see all the main families for each of the neighborhoods in each EP.
Of course they don't come with their houses, so you can work them up according to your little heart's desires.