Automatically dial + transfer

Hi,

We are a group of tennis players that need to reserve four public tennis courts every week. We are looking for a dialer software that could do this for us:
(1) At 5:30 am every Thursday morning, using 4 or 5 Skype out account (or any similar services), the dialer would dial the public tennis court reception.
(2) Once on hold, the dialer would send the #1 pound key tone every 7 minutes or so until 6:55 am to stay alive on hold and not being flush out.
(3) At 6:55 am, the dialer would transfer the 4 on hold lines to 4 tennis guys of us waiting next to a telephone line for the transferred call. Or even best, the 4 guys calls in and pick the line themselves.
At 7:00 am our 4 tennis guys are on line with the reception standing by to make the necessary reservations.

Is it possible to do this with Asterisk?

Thanks a lot for any help.

Richard