My experience in Portland has been lovely, thus far. The community is rich in the arts, with First Friday art walks, a local art school (Maine College of Art), an art museum, and plenty of live music venues. The city is easy to navigate, and the locals are friendly and welcoming. Just last week, two complete strangers assisted me in digging my car out of the snow.
If there were something I could change about the city, it would be the cost of living. Being one and a half hours north of Boston, the city has seen an influx of former Massachusetts residents relocating. Portland has a lower cost of living than Boston, and those who don't mind the commute continue to work there while residing in southern Maine. The abundance of potential renters has piqued the interest of property management companies and landlords alike. In the interest of basic economics, the higher the demand, the higher the price.