Oregon City has more monetary problems than Lake Oswego. The schools are going to be much much worse in Oregon City than Lake Oswego.
Lake Oswego isn't as bad as some are making it out to be. I have lived in Lake Oswego for five years now (grew up on the east side in SE Portland/Clackamas) and prefer to stay in Lake Oswego.
Crime is lower (almost nonexistant) than the surrounding areas, schools are much better(higher graduation rate, better teachers, better funding[both high schools have been remodeled in the past two years]), excellent parks, friendly people, roads are properly maintained(if you exclude the two year Lower Boones Road project), and a very clean city. The drawbacks is that the houses are more expensive than the surrounding areas but not as bad as most think. The reason for the higher housing prices is that there is very little open lots to build on and the city isn't interested in annexing surrounding parcels of land.