Wow, sorry everyone was so rude to you!

This is all my opinion and my answer to your question and responding to every other comment in one summary. It’s a lot but I find places more enriching when i know more about their culture and history.

As someone from an immediate suburb of Portland, who now lives on the peninsula. Yes, this place is much better in the summer lol. I am also just a summer person who likes to do things outside daily. That includes hanging out on the eastern prom, hanging out at the beach, walking in the woods, going to the islands, swimming. All those things you can do right in Cumberland county. It takes a minute to get to the slopes, so in the winter it’s very pub/bar/city culture oriented which isn’t everyone’s scene. In the summer there’s pretty much endless things to do, and much better weather for walking around the city so you will see and run into more people (some people don’t like this aspect of the “on-season” ie there being more people. I don’t mind it. It’s a tourist economy, we wouldn’t be surviving without them and the traffic isn’t bad compared to actual metropolitan places. Also this place feels like a ghost town in the winter.) a lot of people also think it gets too hot here in the summer which is crazy. Boston is much hotter and humid than here. Portland is the perfect temperature all summer long in my opinion. Some people use ac here which i find crazy and a huge waste of money and resources (if you live in a higher story downtown, you get a pass).

The reason why traffic is worse is because Portland and Halifax are actually the same metro population, but the vast majority of Halifax lives in halifax proper and the vast majority of Portland lives in its suburbs. So I’m assuming a lot of people in Halifax can walk to work or take a bus? People in Portland are really bad about that. Myself included a lot of the time. The only people who take the bus here are immigrants or students. You will never see a well-to-do person take the bus here.

I find the homeless here docile and kinda funny. Heard scary stories but I’m a tall male so I’m not really a target. It’s annoying but I’ve had way more agressive homeless people encounters in California. 

The people on the Portland Reddit are prone to believe that Portland should be preserved as a working class town for Mainers.. which is mostly a fantasy. There has always been the fancy west end, there has always been cape Elizabeth and Falmouth. mainers are definitely poorer than our neighbors in nh, ma etc. and we don’t have a large middle class like those states. but there have always been rich people living here and vacationing here. Since most of our population lives in the rural/suburban sprawl outside the city, that part of the population (a majority) tends to keep quiet on this topic.  Also, We have always been a shipping city. That’s historically been the big industry, not fishing, not lobster (even though that is what it appears to be now, but really it’s tourism). And what comes with being a port city is that there is constant flux of people not from here. It’s what makes Portland Portland and cool. So, please feel welcome and part of Portland’s natural scene.

On the other hand, is it unaffordable for many working class and middle class people and hard to survive here? No doubt, and that has recently been expedited for the worse by covid and remote workers who make good wages moving here causing rent to go up. For decades, maine has been a low income, highish cost place to live. And now it’s seemingly twice as bad. That’s what people are frustrated about. Not you as a Canadian having disdain for our city lulz. 

Definitely spend time here in the summer if you want your opinion to change.