I find moving incredibly expensive in time, money, and inconvenience, so I've twice bought "my last house". :)
I think if you can find a place that would work as a solid rental down the road AND you want to become a landlord, that might tip the scales towards buying a smaller rental-suitable place. But, in so doing, you'll give up the capitals gain exemption on primary home sales, so if your area is booming and house prices increasing, that might be a concern.
My first preference/recommendation would be to buy a place you can realistically see yourself living in for 10 years. Not to say that you must do that for it to make sense, but I don't see the logic in buying a 3-5 year "starter home" and doing the moving rigamarole twice (and all the associated expenses).