We're expecting our 2nd child later this year, so we intend to rent a larger space (currently in a 1 bedroom) when our lease ends in August. Due to our requirements for location and bike storage(the commercial apartment complexes around here are surprisingly awful about that), and the increasingly competitive rental market, if we try to minimize overlap there's a good chance we'll have to pay 1500-1700 for a 3-bedroom sfh when we really only need 2 bedrooms and a place to put bikes + trailer.
If we're willing to rent earlier and pay for an extra month or two, then the odds go up that we'll find a suitable place in the 1200-1400 range.
The extra overlap up front would be cancelled out more or less by lower rent. If we end up in two bedroom, we'd most likely want to upsize again in a few years (before FI, when we intend to move to an area with less expensive housing), so we would need to go through this process again, but we'd certainly stay at least couple years.
What do you think? Should we try to secure a place early, or cross our fingers that we'll be able to find a place later?
Just to recap, our main concern is that the supply of bike-friendly two-bedrooms seems to be small and inconsistent.