Billy,

cholesterol is cholesterol starting out in whole foods! the only "bad" cholesterol is oxidized cholesterol and the biggest sources of that are powdered eggs and powdered milk.  most comercial breads, cakes etc. contain one or both so stay away from those!

the good (HDL) and bad (LDL)  cholesterols that you are refering to are cholesterol "packaged" with lipids (the ldl and hdl) by the body for transport in the blood stream.

so in answer to your question eating medium rare meat is only bad in that cooking oxidizes some of the cholesterol in the meat.  but nowhere near as much oxidized cholesterol is present in medium rare as is in well done meat or breads, cakess, cookies etc.