Bostonian, I'm a MA kid at USM (My fourth year here now). I have to agree that Portland is a cutesy town. Not to shift the topic, but the little cities in MA could take a hint from Portland and take some pride in themselves. cities like Lowell, Haverhill, and mostly New Bedford should use Portland as a model of what a smaller city can do to endear itself to people.
My sister came up this past weekend for the first time and when we drove through Portland, aside from the small size, she noted how almost everything on the Peninsula is lit-up and planted, and the buildings are all lit nicely. It's warm and it screams "welcome!"
New Bedford should really try to mirror this. There are so many similarities between the two cities it boggles my mind. New Bedford has a similarly sized University and Community college in the area (UMass Dartmouth and BCC as opposed to USM and SMCC) as well as the pretty coastal setting, historic areas (Whaling District and Portland's Old Port), similarly sized downtown area, ferry services to nearby tourist areas, and both are on highways that connect more populated areas to the tourist destinations.
Yet, when you arrive in Portland, it's very welcoming and New Bedford, well, isn't (aside from the Whaling District). My father and I talked about the lack of chain and mom and pop bookstores in S.E. Mass, and Portland, again, is a good example of what a small New England town can do with this type of business.
That being said, Portland lacks (in my opinion) in two major areas (mostly through no fault of its own): cultural diversity, and vibrant neighborhoods.
Now, I've experienced some different cultures here, but they seem to be more "accepted" than "embraced." What i mean is that yes, there is a relatively large pocket of Somolian population and even a small pocket of Indian population. However, I have seen just one Indian restaurant (there could be a few more, but i haven't seen them and that doesn't mean they don't exist), and I've never seen a Somolian resataurant anywhere. Nor have I seen many international markets, or food stores. Again, that doesn't mean they don't exist at all, but it does show that this diversity isn't embraced as much as it should be.
I'll use New Bedford as an example again. The fishing industry there is huge, and as a result, many Portuguese immigrants have come over to the area. The whole North End of New Bedford closes down for a weekend every year and they turn the streets into a Portuguese street festival. Portuguese restaurants are abundant and so are the markets (Fall River is similar to a lesser degree). Everywhere you go, this culture's presence is felt. The same can be said in Fall River to the Cambodian population. This is not the case in Portland and i think it's a shame as every culture has something to offer. This really leads to a lack of variety in restaurant choices as well entertainment (The Old Port is a small strip of non-descript could be from "Anywhere, USA" venues with the exception of Gritty's, great beer and a Maine staple).
Finally, the lack of neighborhoods kills me. If you want the shops and restaurants, you have to go to the Old Port or right around downtown. It's a shame that there are no neighborhood centers that offer a different variety of shops and eateries in a cluster. Look at Providence, RI for example. You have all sorts of stuff downtown (like Portland), yet you can travel up to Thayer St. and it's a nice, pedestrian friendly drag with all sorts of unique shops and restaurants, same with Hope Street, Atwells Ave. on Federal Hill, etc. This is something i miss as well.
Having come to the conclusion of my rant, I must say that Portland does well for a city of a mere 63,000. Like i mentioned before, certain cities would be smart to use it as an example. However, I find that there is much to be desired and when I finish my fourth year here, I will be leaving (I probably would have gone sooner if my long-time girlfriend wasn't from Scarborough and had roots here that took a while to separate from). That's not to say Portland is a bad place, I just feel that it doesn't have all of what it takes to keep most 20-30 somethings happy for an extended period of time.