Bottom side is child's play; stand tire up - use one tire iron, under edge of rim, pry until shaft is across the tread and then work your way around the rim "tapping" bead off the rim with a 3# hammer, takes 30 seconds or less for anything under 8 ply.

The mini sledge is invaluable; once the top side is off I rarely use more than one iron for the removal of the "back" side and reinstallation of both sides, the hammer takes most of the work out of it.

Jim

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2005 C240 4matic wagon (daily driver)
87 190D - 225K (on loan)
85 190D - 312K (on loan)
2011 Subaru Legacy AWD (Wife's)

I'm having a hard time visualizing what you are doing. Are you prying from the top side or the bottom side (the top side being the side already off)

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1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13

I don't get it either...

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1998 C230 330,000 miles (currently dead of second failed EIS, yours will fail too, turning you into the dealer's personal human cash machine)
1988 F150 144,000 miles (leaks all the colors of the rainbow)
Previous stars: 1981 Brava 210,000 miles, 1978 128 150,000 miles, 1977 B200 Van 175,000 miles, 1972 Vega (great, if rusty, car), 1972 Celica, 1986.5 Supra

From the bottom side. Visualize the tire upright; from what we are calling the "bottom" side put the iron between the tire and rim under the "bottom" bead and across to the "top" side of the rim then lift the iron up across the "bottom" sidewall and down across the tread. You then have a clear shot at the bead as it is tensioned against the "top" edge of the rim.

When we operated the dairy farm, with all of the machinery, cars, trucks, wagons, etc we had 120+ tires to maintain. Even so, I never could justify the cost of a tire changer because either my son or myself could dismount and remount a tire with spoons and a hammer in less than ten minutes.

Jim

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2005 C240 4matic wagon (daily driver)
87 190D - 225K (on loan)
85 190D - 312K (on loan)
2011 Subaru Legacy AWD (Wife's)

Got it.
What was your method of bead breaking?

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1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13

I fashioned a "breaker" bar 35 years ago. It is an old wrecking bar with the curved end cut off. Amounts to a piece of 3/4" hexagon steel, 24" long with a flattened end about 1" wide at a slight angle to the shaft. I rounded the flat end slightly so as not to cut the tire or damage the rim. I put the flat end on the bead and use the hammer on it.

I also have a commercial "breaker" which is a similar bar about 4' long with a "hammer" fashioned from a 30" length of heavy walled 2" steel pipe with a 3/8" steel cap (similar to a steel fence post driver). Slip the pipe hammer over the bar and pound (eliminates the chance of missing the bar as with a conventional hammer and makes it easy to direct the force). I use this bead breaker primarily for larger tires (20" and up) although it will make short work of a difficult 16". Also works well on heavier tires (we have some 12 ply wagon tires that can be a bear to break down).

__________________
2005 C240 4matic wagon (daily driver)
87 190D - 225K (on loan)
85 190D - 312K (on loan)
2011 Subaru Legacy AWD (Wife's)