My Rav used the car analogy as an analogy for his halachic psak that the broad restrictions are not halachically valid (obviously there was more to it than just that). So I would follow the daas torah of the Rav, even if you dismiss the argument based on your laymen's assessment.
I was in the ER with my father (who was unconscious at the time) after he had a cardiac arrest and the head doctor said, "Leave him be, don't do anything and let nature take its course. He is older and what would be his quality of life even if he survives?". Needless to say, we ignored the doctor and G-d willing my father this week will be attending his 8th grandchild's wedding in the 5 years since. This is not an isolated case of doctors sharing such advice, look at Chayim Aruchim's website and you will see this is a prevalent conventional wisdom within the medical field.
My point? Just because doctors say their opinion doesn't make it daas torah. Do they take into account the value of tefilah b'tzibur or pilpul chaveirim in yeshiva or learning in shul? How about the geulah that can be brought about by being mesameich chason v'kallah or the power of a bracha someone can give or receive at a wedding? Zoom as a substitute is marginalizing the value of Jewish communal life. Where these world changing powers stand in a case of pikuach nefesh is for poskim to determine. But it is not right to dismiss them as frivolities of Jewish cultural life that are readily expendable. The polar opposite responses of MO and chasidic/yeshivish responses may have something to do with this equation. Noone wants more deaths, but some would be moseir nefesh to a greater degree than others for these core values.
As to dina demalchusa, where I live the government restrictions for shul were made tighter as a balance for allowing indoor dining. The lead poseik in town said that dina demalchusa dina does not apply since it makes no sense, and the very restrictive Vaad HaRobonim followed his psak.
If I'm reading this correctly, you have 3 points: a) your Rav gave a psak for your city that the local EOs are not valid al pi halacha, b) Jews value life more than the medical establishment, and c) Jewish communal life has a value so great that we should be ok taking certain risks in order to preserve it.
Regarding point A: I don't doubt your version of the realities in your community. However, you have to understand that an anonymous DDFer posting about an anonymous Rav in an anonymous place giving a psak that isn't on paper... it just doesn't carry a lot of weight. I have yet to see a psak
on paper by a Rov or BD explaining why EOs can or should be ignored.
To point B: I wholeheartedly agree with this sentiment. However, the facts on the ground seem to contradict this. When doctors are asking us to take certain precautions in order to keep people from getting sick, and we blatantly ignore them because we know better, it sends a contradictory message. Why is it that once someone is sick Klal Yisroel moves heaven and earth to help them and keep them alive, but when it comes to keeping people from getting sick in the first place, we shrug our shoulders and say "acceptable risk?"
To point C: we're past the point of shuls being closed in almost every place. Tefila b'tzibur is not at risk. Learning in a beis medrash is not at risk. We may need to limit the amount of people in a room at a time, but that's not new. There have been fire codes and capacity limits since the 1920's. Masks don't prevent communal events. They may be uncomfortable and inconvenient, but they are stopping Jews from doing what we feel is essential to our Yiddishkeit.
So really the only point of contention here is weddings. Let's look at that for a second. According to the science available to us right now, there are certain settings which have been documented as being responsible for spreading the virus at a very high rate. Restaurants are one; bars and nightclubs are another. In general, indoor gatherings present much more risk than outdoor ones. Without c"v comparing the holiness of our weddings to these other settings, we have to acknowledge that the functions of those settings are replicated at our weddings. There is loud music, drinking, singing, dancing, eating, prolonged contact at tables without masks, and all in indoor settings. Turns out, the things that make our weddings great also makes them hotspots. And you don't need to be a scientist to see that since Tisha B'Av, we've seen a very noticeable uptick in cases, almost always traced back to weddings. So now that we've ascertained the risks of our weddings, independent of EOs, how can we justify putting people's health at risk in order to be mesameach chosson v'kallah?
Anecdotally: there was a wedding near me last week. There was a Covid exposure from someone who wasn't wearing a mask, ironically, from CA... because in FL we need to import our exposures. The whole family, including chosson and kallah, spent a very miserable shabbos sheva brachos at home, scared for friends and family who may have gotten sick. I don't care how happy you may be making the young couple at the wedding, it can't outweigh the feelings of the next week or longer if people got sick at their wedding.
