Hey Smasher,
I'll give it a shot. I have lived in Austin and Portland. I started cycling about 2.5 years ago in Portland (SW area - Lake Oswego). I commuted and rode year around so I will start with the weather.
October to June (Nov-Feb the worst) expect to be spit on just about every day (I only got drenched a few times). Temps avg. 40-55 during the rain. It will swing much lower if you get some of the clouds clearing (but hey you get to see the sun... perhaps).
1. Bike with full fenders & extra extended flaps
2. Good light weight rain jacket with venting (undergarment and jersey)
3. Rain pants (optional) I have them and use them sometimes... Usually tights/knickers or leg warmers
4. Booties (as water resistant as possible)
5. Full fingered gloves that are water resistant
6. Good light (good one!!!) and blinkies (it is just dark... even during the daytime in late fall to spring) and you want to be seen.

While it can be crowded in Portland (urban growth boundries) for the most part has very aware vehicle drivers and lots of bike or MUP around. While the direct routes might be sketchy - a slight detour will most often give you a great ride to where you are heading. A lot of bike routes will have you in the countryside within 5-8 miles from just about anywhere in the city.

IMHO - Portland is VERY bike friendly and aware

The locals say never let the rain change your plans and they mean it. Riding in the rain is expected and if you want to ride get used to it. Everyone else does.

Once you hit March the weather starts to slowly shift to "slightly better" and you will get a couple of good days mixed in. July starts the "Golden Days", from July to Sept. Portland is awesome. Typical lows in the 50's and highs in the mid 70's with day after day of clear blue skies.

An average 30-35 miles ride will have 2000-2500 feet of climbing (per garmin edge) and you will have the ability to do extended climbs of 4000 + feet (bridge on Stark to top of Larch Mountain) which is really alot of fun and many more great climbs (what i think I will miss most)

Do cycle Oregon if you get a chance.. just goggle it ;-)
Ride with the guy's at Lakeside Bicycles in Lake Oswego (Good People!) Sat & Sun 9am or 9:15.. uhhh or9:20 lol sorry could not resist...

Ok... sorry too long... Now Austin... Keep in mind I have only returned recently and now as a cyclist. However, I have been actively comparing the two cities because I am interested how Austin will compare.

Weather, Austin will have more sunny days than you can shake a stick at and the majority of the winter will have big temp swings during the day. It can be freezing in the AM and 70 degrees that afternoon. Summer can get very hot..... You will need to ride in the early AM if your not into 90-100 degree riding.

In the last week I have put in about 130 miles and have to admit I was a bit surprised at the amount of climbing I have done. nothing substantial bit lots of rollers and more rollers... Austin is on the edge of the Hill Country so you will also get some shorter and steep climbs (but nothing extended like the Pacific NW).

So far I have seen less bike lanes in Austin than Portland and the vehicle awareness seems a little less tolerant (keep in mind the low mileage I have put in so far).

Austin does have many more roads with good shoulders that are great for riding on (2 abreast with ease).

Couple other things:
Portland: state income tax, bottle and can deposits, smaller state population (aprox - 3.7 million), more expensive for groceries etc., housing is expensive to buy.. (but I have a house for sale in Lake Oswego if you are interested lol). These things and the lack of sunlight pushed me over the edge and I left for Austin.


Sorry about dragging this out and I'm sure i missed a few things... but hell you asked...

I'll keep updating you with my experience here in Austin as I spend more time in the saddle if you are interested.

Dave