Shalom and thank you for your question!

To answer in a nutshell the questions you asked that touch on many aspects of faith and trust in G-d, where it begins and ends, and what it achieves, we would have to say that the answer is different in every individual circumstance.

There are guidelines however.

The concept that you were told is  Jewish  – ‘Love your problem and it goes away’, is true sometimes, perhaps when we are talking about a problem that has to do with one’s personal approach to life and people, and one’s pattern of reacting to circumstances.  If I have had a tendency till now to procrastinate, then ‘loving the problem’, meaning, accepting that this is a challenge that G-d gives me in order to deal with it, can help me come to terms with it and eventually overcome it. If one has  G-d forbid suffered a tragic loss of a loved one, or loss of a

limb for example, that problem will not go away because I changed my attitude.

The Sages indeed teach us to thank G-d for everything that happend to us, painful though it may be, as you point out. The Jewish practice is to say ‘Baruch Dayan haEmet’, ‘Blessed be the Truthful Judge’, when someone dies. This will not bring the person back to life, but it will put our awareness into perspective, making us realize that it is part of the Divine Plan, even though we don’t understand it. But what if I asked G-d to send me a particular good or pleasant thing in my life, perhaps even a basic need, like bringing a chld into the world? It may be taking many years of stressful waiting and it isn’t happening yet. How do I deal with this? Here, as you point out, I must believe that everything is for the good, while concurrently doing what I can, with the guidance of Rabbis and medical experts, to make a ‘vessel’ for blessing. Sometimes the blessing will materialize sooner, sometimes later, sometimes not at all in a direct fashion. I need to constantly work on my faith and trust, accepting what G-d sends, but this work itself is a means for bringing down the blessing. We’ll speak more about that…

You ask if G-d might not leave me dealing with my trials and tribulations since I’ve adapted to them so happily…. Here we can take an example from our Patriarchs and Matriarchs. Yaakov (Jacob) , on his way to Lavan, rests in Beit El and then has a conversation with G-d. He promises to be the faithful servant of G-d  “If You will give me bread to eat and clothing to wear…”. We are taught that Yaakov was an extremely righteous Jewish leader, a very integrated personality, one of the Patriarchs who chose to be a shepherd so that his occupation would give him time for contemplation and prayer, rather than having to deal with the nitty gritty of worldy affairs. How does such a personality request such mundane things from G-d? The Torah teaches us that we must ask G-d for our needs, and also trust that He will provide them. If we don’t have food and clothing, we won’t be able to perform the commandments as G-d requests. It’s a two-way street! Along these lines, Chana, the mother of the prophet Shmuel, prayed to G-d for offspring. In her inspiring prayer, she points out to G-d that He has given her the feminine potential to carry a child and nurse it, is it for naught? She also promises to give up her child to serve G-d in the sanctuary, which is what happened. She wanted to bring a child into the world to serve G-d, and her prayer was answered. Yes, G-d does want us to be happy, to answer one of your questions, and when we align our aspirations to those that G-d has for the creation, as Chanah did, we are increasing our chances.

Going back to our forefather Yaakov,  on his way back to Canaan from  Padan Aram, now accompanied by the family that he has built up with G-d’s help, despite Lavan’s machinations, and anticipating meeting up with his wicked brother Esav, (Esau,) he becomes worried. Esav is approaching with 400 men. Yaakov splits his family , servants and flocks, into two camps, prepares gifts to appease Esav, and prays. Why is he concerned? G-d has come through for him, granted him wives and children, along with much prosperity. He is concerned that perhaps his merits have been used up, and he no longer deserves G-d’s kindness. The Lubavitcher Rebbe teaches us here that this approach was lacking. What was needed here was to trust in G-d nevertheless. Why? The act of trusting G-d in itself makes a ‘vessel’ to draw down blessing. It isn’t easy to place our trust in G-d, that’s why when we overcome the difficulty and trust nevertheless, we are creating a new spiritual entity that gives G-d a ‘reason’ to want to help us.

Hoping this answers your questions to some extent!