It’s a little hard to find decent cigars for less than $10 unless you are buying online. A cigar that costs $5 in WI costs $10 in MN due to our wonderful taxes.
That being said, the Olivas I just picked up cost me $29 for 5 of them and they retail for around $8-10 in stores.
Arturo Fuente have some cheaper options that most smoke shops have, Punch, Macanudo, and Romeo y Julieta are all solid at a good price point. Are there better, certainly, but for the cost of their “regular” lines, they are some of the better ones at that price point. Also don’t be fooled that the maduro (darker) cigars are higher in strength. Some are, some aren’t, but its a different flavor more than anything. In my experience, the lighter colored cigars are slightly creamier, peppery, and spicy, while the darker cigars are more earthy, chocolate/coffee, and creamy flavored. I’m more of a maduro fan. But try as many different kinds as you can. It’s like wine or whiskey.