How can I address my career future with my current PI?
Your advisor has the duty to inform you if you are meeting expectations, and to notify you in a timely manner if your contract will be renewed or not. Politely bringing this up at the end of the meeting should not cause conflict with your advisor—unless your advisor is a control freak (in which case it's not exactly a bad thing that you'll need to move on!). 

However, I would have this conversation as soon as possible, as the end of your contract will be here quite soon. You should inform him, if you'd like to continue working with him, that such is the case. You should also politely mention that if the finances aren't secure for a commitment, that you will need to consider additional job opportunities to ensure that you are not "stuck" looking for a job without a current source of income.