- Should we feel good about our lives?
Yes, we should feel great and happy about our lives, Buddhism is about feeling happiness. By that I mean that while dwelling in moments we should know whenever we are happy - awareness of that is the very thing that makes us notice and store positive seeds for the future. Without that, of what possible help can we be to others if we are miserable, useless and confused? Conversely, when we are afflicted by negative emotions we should know that too, so we apply skilful means and let go of them, or not to produce negative karma as the result of them.
Acknowledgement of pleasant moment and happy life needs to be made without any obstructions - by just noting it. Remember that great deal of suffering is inflicted upon you when you torment yourself by asking and questioning such questions as you've asked; Should I be feeling happiness and joy at the given moment? Should I be happy about life at all? That is because of the fact that we take things to the extreme, drifting off from the path of Right effort. Hence, we have to re-adjust from time to time, until strings play well. You should not feel bad about feeling pleasure and enjoy it while it lasts, just note and contemplate that it is going to end, because nothing is permanent, not even life. Such antidotes to pleasure and excitement will save you some disappointment of thoughts like "I'd rather this gig last for much longer, it was such a good set...", "I have lost my puppy, and I loved him so much...".
- Can we be both Happy about our life and pursue Nibbana?
I would attempt to split this into a two-step process. Firstly, we sail off, and that means we have Eightfold path to establish solid base of happiness and bliss through good karma and release from cyclic rebirth, in order to reap positive things in future. It is like training wheels that one cultivates while pursuing more sustainable, unconditional ways of higher bliss. Those unconditional are Dharmadhatu, Rigpa or Jhana - they all speak of the relatively same great experience. So, then it comes the next step we arrive at some realisation that is the resultant of right mindfulness, concentration and effort - all the things resulting from insight into no-Self, impermanence and Emptiness. It might be like above, the first contact with Jhana or just getting in touch with Selflessness. Because mental discipline is a very long process that might take lifetimes, thus the reason for the initial path of ethics has to bring us solid happy foundation quickly, long before realisation, and long long before we reach the other shore to become unafflicted completely.
Since laypeople don't have as much time as monks, even some realisation of three marks of existence is enough to provide sustainable source of happiness. Most importantly, pursuing Nibbana should never be forced or pushed. Insight and realisation should arise naturally in time.
Therefore, knowing that true happiness is unconditional we should not attach too much to the plans of making ourselves happy by conditional means. If such things happen OK, but keep in mind they're not reliable. Constantly looking at the other the shore should give us enough to be wise about it, and try our best not to attach ourselves.
- If we only look at life as suffering and unsatisfactory does this not
make us masochist?
Yes, if we only look at life like this, we are in fact masochists. Life is not all suffering, remember. I reject Four Dharma Seals in favour of Three, they are more truthful. Read: Maha-mangala Sutta: Blessings, this is how joyfully we should approach Buddha's teachings for they give great happiness in our hands. If Buddhism makes you feel like this, it is not Buddhism making it miserable, it is you! Remember it is not things but reaction to things that make us suffer.
