[quote=NotALizard;9688678]
I guess the cost of rent depends on the size of place you are looking into. I might be putting my house up for rent in the next couple of months. It is a 4 bdrm, 3 bath in an excellent location for $1600 per month. Anacortes is another city (off the island) across the Deception Pass bridge and is also a nice area to live, but a little further drive with a higher cost of living.
Oak Harbor winters aren't too bad. Be prepared for snow, not heavy snow, but snow nonetheless. I have been here for two years and the most snow was 2-3 feet. A good amount, but it doesn't stay around for long.
It takes some getting used to the weather if you move here from a different climate. I guess the time it takes to acclimate yourself to the weather will depend on the individual, some people never acclimate. Some acclimate in months, it took me a good year to get used to it. I am from the desert (Imperial Valley) I was used to dry and hot, here is cold and wet. Except for the summers, which are very short, but incredibly beautiful. Lots of outdoor things to do such as, camping, hiking, fishing, biking. Gorgeous scenery. Spring is rainy and the fall is cold and rainy. There is also a good amount of wind throughout the year.
Good news is that you wont have to spend as much for A/C, don't really need one here. BUT you will probably be using your heater a lot, especially the first year.

Hope this helps.