The one constant with tools is that they wear out with use.
While worn bearings and bushings may require replacement of the component, if not the tool itself, other wear is easier to deal with. Such is the case with cutting and drilling tools.
While you may not be able to guesstimate how long before they need to be sharpened, you can be assured they will. So, when you buy a tool, think maintenance. What parts will need to be maintained? Can you do the maintenance, or will you need it done for you? How easy is it to access the parts to be maintained?
This was recently brought home to me when my wife's favorite trimming shears began to jam more than they cut. This particular brand was easy to disassemble. One screw undid the two shears, allowing one to swing away and be removed. That made the next step of sharpening a breeze. I had full access to the beveled edges.
If you don't want to do even minimal maintenance yourself, ask the retailer you're dealing with if they handle maintenance and repair. This may rule out big box stores and the "lowest" price.
However, knowing your local hardware store does sharpening and other maintenance can make a higher up-front price look more reasonable. Sure, you can ask your local retailer to repair that tool you bought at the big box store or through the Internet, and they may do it. However, if you never buy anything from them in the first place, will they be there when you need your things repaired?
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