Originally Posted by corporate-wage-slave

Welcome lrlrip to Flyertalk, and welcome to the BA forum in particular. It's great to see you here, thank you for the question, and I hope you will continue to make use of this valuable forum.

You do need to earn the 300 TPs and 2 flights within the span of one membership year, and the dreaded wiper comes through on 9 September every year. So if the return is afterwards this will go on to the following year. If you think you can make good use of Ruby, mainly the 7 days of advance seat reservation, you may want to add a few cheap trips to Europe or even a very inexpensive flight whilst in Orlando. An awayday from Orlando to Miami in First will net you 120 TPs return for example, and there are other options (e.g. going to Orlando indirectly).