I am trying to find out if I can download lightroom and pay the $9.99 for the yearly contract however within the next few months if all goes well, I am hoping to have a new laptop. Will I be able to transfer and download again or would I have to cancel (then be charged the 6 months) and start a new contract with the new laptop. Thanks!
No, just install the creative cloud application on the new machine and log on using your adobe account and you should be able to install direct from there without uninstalling from your previous machine. You can have it installed on multiple machines, you just can't simultaneously use it on more than one machine, which is why it makes you log on to the creative cloud.