Primary Residence. How nice should it be?

[Sam German]

Hey Everyone,

My wife (22) and I (22) own a primary residence in Blaine, Minnesota (large suburb 20 mins north of the cities) and recently purchased a rental in St. Cloud (1 hr NW of cities). I want to keep pushing, and my next idea would be to find another primary residence and move there, taking our roommate with us. We would then turn our current home into a rental. 

The Dilemma I face is this: My price range is $275k - $350k, but I struggle to find something nice enough to want to live in, that would also cash flow once we move again, turning the home into rental #3. I don't know any contractors at all, let alone ones who won't give me the shake-down. Therefore, any homes that need a lot of fixing, even cosmetics, might be out of the picture. I just don't know if there will be renters who are willing to pay over $3,000 for a nice home in the 'burbs, otherwise, my new primary residence won't cash flow when I move out.

TL;DR Has anyone had success buying a nice primary residence and finding renters to cashflow when you move out? Or will I have to settle for a light fixer-upper?