Also, we'll be calling some management agencies about rentals very soon but in the meantime wanted to find out the Pros and Cons of the various downtown Portland neighborhoods (NE, NW, SW, SE)
well i can't say much about the pre-schools as i have no kids...
as to the neighborhoods, without knowing what you guys like and what you value it's really hard to recommend anything.
Portland has so many different neighborhoods that are great - but for different reasons.
do you want "family" urban, traditional suburban, artsy, "happening"??... it's all very difficult to guess. and coming from NYC i have no idea what your expectations are...
to be VERY general, i will try and describe the overall:
downtown is downtown (ok, not even close to Manhattan!) with smaller apartments and lofts... actually pretty affordable but probably not the best for a family (although 2 friends of mine with a 2-year old lived there for a while)
inner Northwest (where i lived - NW 23rd and Glisan) and Southwest are VERY nice - happening as well quaint - close to downtown, the river and the hills... but pretty pricey... this is the prettiest park of Portland AND close to downtown so it is understandable.
further West (the other side of the hills "skyline rd") is more like traditional older US suburbs... wider curvey streets, more open space/trees, larger lots, etc. Beaveton is one of the "hippest" suburban areas without being super-expensive (like say Lake Oswego). further west is more and more suburban but still nice. Beaverton is a good compromise - it's relatively bike-friendly, close enough to bike-commute to downtown (or combine with Max)... further out like Hillsboro or something _I_ would not recommend, but then i don't like the "new suburbs" -- i know there are a few happy Beaverton members here like John Radcliff (spelling?)
North portland used to be the "bad" areas but is now being gentrified... i have LOTS of friends who have bought houses there. schools might be a problem (no idea) but the area is nice and close to downtown.
further North across the river - Vancouver WA i would NOT recommend -- this is very un-Portland as it is auto-centric AND they are anti-tax so their schools suck (my coworker was always complaining about how they had downvoted ANOTHER school funding proposal)
the East side is a whole 'nother animal: in general it is less expensive and less ritsy, but not in a bad way. close to downtown is very artsy/happening and where a majority of Portlanders prefer to live (Hawthorne). the further east you go, the more "suburban" but not really - only in the old 50s way - more families, less "happening" but still lively communities, quaint, safe and good for biking.
and there are some good "suburbs" to the Southeast which each have their own flavor. a few are comparatively bike-unfriendly but many are not - can't really give specifics.
just guessing: for a family look in either Beaverton area or the East Side depending on your style... as long as you're not WAY out of the city (like say Sandy to the east) for a serious Utility Cyclist you should be able to bike commute to work without much trouble...
P.S. my info is also out of date as i haven't lived in Portland since 2000... (but geography is an interest of mine - i left portland to start my PhD in that field)