Insimenator.org

Question 1: Let's say I have 20 different lots in my neighbourhood, all in different seasons after playing them for a while.  Now if I set the seasons for that neighbourhood to winter-spring-summer-fall, does that make all the lots change over to winter?

I am hoping that only new lots will start at winter and all existing lots will retain their current season.

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Question 2: if a family is moved from one lot to another, do they start over at the first season or continue where they left off?

I want them to continue where they left off.

I'm not really seeing what help you need here.  Is there a reason you can't try the things you have a question about, and see what the results are?  It will either be the way you want it, or not be that way.  Logic says what you would like to happen would be the expected result.

From what I can tell it resets.  I changed all neighborhoods to what I felt was logical.  Fall, Winter, Spring then Summer.  Went back to lots that I left, and it was the beginning of Fall.

I would imagine that cwurts00 was asking because there may be someone out there who has done this and knows for sure - it's always nice to know that something will happen rather than doing something that you're not sure of the consequences to a neighbourhood that you've worked hard on.
 
The only experience I had of this was in the new neighbourhood - Riverblossom Hills. I changed the seasons when I started the neighbourhood but the Maxis families were still in the seasons that Maxis left them in
 
As for the families - the seasons are specific to the lot not the family, so if you move a family into a brand new lot then the season will be the 1st one you have set for the neighbourhood.

It will reset the hood and all the residential lots.  The proper way to do it if you do not want it too reset everything is the 1st time you load your hood, you set the seasons BEFORE you start to play any of your lot again so depeding of how long you will play each lot they will end-up having  different seasons.

There is also an aspiration reward you can use to change the seasons on each of your lot, so maybe your best option if you do change the seasons order is to use that reward to set each lot you play individually.

*sigh* the only one I was smart about it with was my Uni neighborhood. I set it to have an extra fall and no summer (they are out of school during the summer :) ) because fall helps them learn faster.  Unfortunately, I didn't change the Maxis/EA defaults on the others and it was fall for EVERYONE. Since I don't play any one family for long periods of time, I'm really tired of fall. So I changed one neighborhood and over night the season changed for each family.

Hope that last helps you.
~dizi

And as of your question #2, they will reset to the 1st seasons when move into a new lot.  

If I am not mistaken it is the lot that keeps memory of the seasons it is in, not the family itself.

Again, you can use the aspiration reward to set it otherwise.