Shalom.

You have asked several questions, so let's see if I can answer all in a brief format.

 

1. Olam Habah.

The crux of the question for olam habah is how you interpret the term.

If, by it, you mean another world, or some sort of life beyond the grave, I would say that most Reform Jewish thinkers would answer "no". This goes back to the ideological (and theological) position taken rejecting resurrection as a tenet of Judaism in the period of Classical Reform. I am not able to cite any studies showing general belief today, but the Reform rabbinate seems not to be unified in their approach to this question, so perhaps it is in flux.

On the other hand, if you mean by olam habah 'the world that is coming'; in other words, the improvement of this world, then I would say that most of the Reform thinkers would agree that this describes hopes for a messianic age (a time of peace for all, with no hunger, no poverty, and no oppression), and there would be general agreement that such an olam habah would be a possibility, and certainly something we should aspire to and work towards.

 

2. Living up to what is expected of you.

The Reform movement historically has emphasized the ethical and moral aspects of Judaism, especially as set forth in the Prophetic writings, so this question is in keeping with that approach. A fairly straightforward measure of this would be to conduct a self examination, and determine if you are acting justly and with kindness, supporting those around you in need, and making the world a better place. In this way of thinking, the instruction of Torah is the guide and the baseline, setting forth the goals; the details of how you are to do it are left to you. In this way of thinking, you are doing what God expects of you (if you believe in the divine origin of the Torah) and what you should expect of yourself as a human being, when you act in accordance with these principles and values. As a side note, this is the focus of the month of Elul and the Ten Days of Awe - the period leading up to Yom Kippur (the Day of Atonement), when we engage in introspection and examine our deeds in the past year. 

 

3. God and God's Nature

I think that the jury is out on this one. Again, historically, at least some of the Reform movement's formative thinkers were uncomfortable with the idea of a personal God, and made some changes to the liturgy to remove that language, but as time has passed, that view is less clearly universal, and may be shifting (as I perceive to be the case in Reconstructionism). I do see many of the 'Jews in the pews' praying quite personally when they encounter a crisis; I am unsure what they think when things are going well for them. There has been movement in the Reform ranks towards more traditional ritual practices; perhaps this is also reflective of the view of God. 

As for God's nature; I don't think there is a singular answer. Not for Reform, and probably not for Judaism as a whole. Perhaps the most commonly used analogy is God as a parent, however, God is depicted in the Tanakh (Hebrew scriptures) in multiple ways, and in Jewish thought the concept of God has changed and morphed over time. Even within the Tanakh, God is seen in many ways: angry, jealous, kind, loving, and a warrior, to note just a few. There is no single presentation, and no agreement on the nature of God. 

 

 

How do I measure whether I'm living up to what God/I expect of me?
Ultimately, only God knows for sure whether one is living up to what God expects of that person, and we will only know for sure when our souls are in God’s presence in the world to come. However, God gave us Torah and its mitzvot in order to guide us in the proper direction.