I look at the movie "Groundhog Day" like I do, "It's a Wonderful Life"

Both of them are positive; eventually what you are "learning"/experiencing with the crappy side of life is going to come in handy or turn around and all be "right".
Have you read any C.S. Lewis? I love his book,
The Great Divorce when it talks about how "attitude"/belief have so much to do with things and when things finally line up (like they did for Bill Murray) all the old, bad stuff takes on a new meaning and one's understanding of what they were for/about makes it all good in one's past. That's actually been a lot of my perception now (I'm 60) after a hard growing up and many years of therapy, etc. The heartbreaks of my life when I was 20 now make sense to me (the only person to whom they matter) and don't hurt anymore.
I have two cats (am surrounded by dogs with most neighbors, I live on the water :-) and they're 10 years old. A couple of years before I got them, I had another cat who died at around age 18, whom I had taken off the street when he was about one and a half. I can look at that cat and the cats I have now and clearly see what I have "learned" about myself and life through those cats; how I ended up with "those" cats, etc.
I wish I could think of a way to comfort you with your lack of money, health, and companion/dog problems but that's a puzzle I still can't do for myself; I look back on my life and ask what I would do/have done differently; I was in about your situation from the ages of 7 to 35. I am in awe, looking at my stepsister's life (she's 13 years older than I am) and my life side-by-side, she had an idyllic lifestyle until she married and then had hell before coming out the other end 10-15 or so years ago.
The only "hope" I can offer is that it does keep changing; yes you're going through the idiot first part of the movie now where he drives off cliffs and steals the groundhog and does other things that make no difference but then, though they
seem to make no difference he comes up with a plan and learns to play the piano, judge the moment/consequences of each action, etc. Remember when he tried to save the old guys and how you hoped that would work but it didn't?
It's all a learning and doing-the-best-we-can life-long situation. No, you might not be "rewarded" by doing the best you can but there are larger schemes at work that we can see right now when we're working in them. I will never forget my 20 year old college roommate who had just become engaged "describing" for me what my future husband would be like and how I took that memory with me through thick and thin until I was proposed to when I was 38!
All I can offer is advice to do the best you can and try and stay facing "forward" because one does not know what is coming next down the pike but it could more easily be "good" than "bad" if one is in there swinging the bat at the balls. Yes there will be a lot more strikes and balls but the possibility of you hitting the ball because of your "work" each day is much greater than the possibility of the ball hitting you and injuring you!