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As a general rule handheld radios will talk up to 2 miles line-of-sight. Anything you place between the two radios will reduce range. Talking from inside a building to outside, you can expect 1/4 to 1/2 mile. This being said, a radio can talk as far as it can see, so if you were on a mountain top, you could conceivably talk many miles into a valley below. Height and placement of your antenna determines range. Holding your antenna upright perpendicular to the earth will give you the best range.
A few things you might check: 1) Be certain the radio is turned off when plugging in any audio device. 2) Be certain the device is plugged in all the way. You should feel it seat, or click into place. 3) Use a device designed for your model radio. Aftermarket accessories don't always have the functionality of the OEM device. 4) Be certain you have special features such as VOX turned off on your radio.
The T5500 is a 2 channel radio and the T5725 is a 14 channel radio. However, the radios should be compatible with each other on FRS channels 1-14 as long as both radios are using the same Quiet Talk code. If the Quiet Talk settings are different the radios will not be able to communicate with one another.
Assuming all settings are the same (as you say) and the units are within range of each other (typically less then a mile over clear, level terrain) they should work just fine.