Are the listings in the higher rent range getting any traction? How long have they been on the market? Is there any price movement down? If they are listed for rent through Zillow you can see the number of contacts and applications.
If they are getting traction and moving quickly, and your house is comparable, then you have a decent chance of getting the top of market rates.
Just like for selling a house, I’d highly recommend getting quality pictures taken for your listing. High rent + bad pictures = sitting on the market.
To your second question about buying another property and breaking even… I would not assume you’ll profit or break even by simply gauging rental rates and mortgage payment. Are there any major capex expenses looming? Roof, HVAC, water heater, plumbing? If anything major is looming in the next 2-5 years that could quickly put you in the red. If you can afford that, great, but no need to put yourself in a risky financial position by buying another property if you can’t.