Transmission works with wires but not always with wireless

[dhouston]

I am using the digital data output pin. Also, since I need to send my data 5 times and with a pause of 5 does it mean that I should make my preamble longer?

I would use a 5ms pulse as the preamble and a 20ms pause between data packets (it allows the AGC and threshold to reset).
On the receiving end I would use PulsIn to wait for the 5ms pulse and then go into the normal receive routine once it's received. Using some type of error detection (e.g. checksum) is a necessity.

What range do you need? How much data do you need to send?

Looking at the digital data pin with a 'scope (or recording it with a soundcard as I suggested earlier) can eliminate a lot of guesswork by telling you whether your signal strength is adequate. I find it invaluable.