looking to rent a SF house in Mildford, CT/advice on rental mrkt

[Curran D Bishop]

I'm looking to rent a SF house in Mildford, CT (Connecticut) and am wanting to get a sense of the rental market in the area (New Haven, Bridgeport, Stratford, West Haven, Hartford). We want to get to know the area a little before buying either a house hack, or possibly a straight-up investment property (and continue renting our residence).

I'm brand new to the forums and not sure if this is the place to be posting this...

I'd like input evaluating my plan (rent while getting to know the market; buying a single family house with detached apartment to use as an AirBnb, or possibly buying a du-tri-plex as an investment while continuing to rent).

If we're hoping to move in mid-December, how early can we realistically take a house-hunting trip? How reasonable is it to ask a landlord to hold a property for a few weeks for us to move if we put down a deposit but ask for a start-date a few weeks out?