Cigar Monster (part of Famous Smoke Shop) has rotating deals every hour and then also have all of the daily deals "Monster Mash-Up" available for 1 hour twice a day 11-12 ET. Occasionally they have Monster Mash-Up all day. Most of the deals are 5'rs and frequently come with free shipping. I think you will find quite a few deals there in your price range.

The Oliva G Natural (Cameroon) might fit your bill for mild-med with a bit of creaminess or the Oliva Connecticut.
Flora de Oliva
Perdomo Reserve Champagne Connecticut

The Two Guys Smoke Shop has their own labeled Dos Hombres Dominican, which for the price of a shade over $2 apiece, isn't bad, especially for working around the yard. Decent flavor and construction, maybe a tad light on the fill, but can't complain for the price.

Occasionally you can get the Arturo Fuente Double Chateau (Churchill size) for around $5 ea. Consistently good construction and a pretty good cigar.