In my experience, prices tend to bottom out for leases starting June 1, but that was pre-pandemic so ymmv nowadays. You're going to have a hard time finding a place that meets both your price + QoL requirements -- studios are easily ~$2k these days, and a 2br/2ba is $3500+. Allston/Brighton might be an option, given your willingness to bike, and while we're flatter than Seattle, we're much colder and our precipitation tends to accumulate a little more.