Well I certainly don't mean to discourage you, just wanted to give you some hopefully useful insight.
You are right, there are those who like Portland nightlife the way it is, and then there are those that want more. Either way, even those who like it the way it is would be happy with more, so you don't have to worry about overdoing it. Its just that its such a small market that experimental places tend to either be a success or a dud and nothing in between. There are some nightclubs here now, and some are pretty successful. There have been a lot more in the past, most of which got shut down due to violations, not due to lack of demand. I think a new night venue would be welcomed. Sometimes the scene is pretty lame in the winter, but then again in the summer months it can be more packed than some of the bigger cities (by virtue of being so densely populated in the old port, whereas some larger cities have their nightlife spread out, so even if its "better" the people watching isn't as good. People watching in Portland is almost second to none).
I'm glad to hear you are into urban development as well, this is the right spot for you. I wasn't saying that Portland is somehow LESS of a city than Boston, I was just saying the two cannot be compared, which is something many people try to do. Portland and Manchester might be able to be compared, but not Portland and Boston, and I was just pointing that out, not so much to you as just in general. I like Portland for its distinctions from Boston as well. Although I like Boston for the same reason, its different than Portland.
As far as development and redevelopment in town goes, I'd be glad to discuss it with you at any length you'd like. Its safe to say I am obsessed with urban development, and this is particularly so with Portland because A.) I am most heavily effected by the goings on here, and B.) because it really has a lot to work with, a good foundation for continued greatness in the region.
So as not to overdo things, I'll just give a brief synopsis of things going on in town currently, and if you want any more specific detail on a project or neighborhood I'd be glad to share as much as you would like to hear.
In the Eastern Waterfront (adjacent to the Old Port) things are currently on hold. One major project is tied up in litigation between the developers, and another is waiting out the economic recession. a major (for Portland anyway) new hotel just opened and really adds a lot to the character of the neighborhood. A new cruise ship terminal was built to draw investment to the area, but the ship for which it was built just canceled service to Portland, making the neighborhood's future less stable. And the planned construction of a major westin hotel and condo center waited to see if a rezoning at the Maine state pier would effect the market for the type of consumers it was targeting, and then the economic recession canceled those plans. the site is under contract with a new buyer, but no plans. The maine state pier had two proposals result from a lengthy RFP process, both of which failed to materialize. thats about all i can think of at the moment, although there are additionally plans to build a small office next to the new ocean gateway garage in this area, and there are some abandoned buildings of an industrial character further up munjoy hill that have been part of ongoing discussions to extend the old port east. just talks though.
then there is franklin arterial, which is a major intown thoroughfare, which is being targeted for redesign, and the city wants to make it look more like a toned down version of congress street. There are a few large open parking lots at the top of this street and in the past 5 years there have been proposals for 10, 15, 17, and 30 story buildings on these lots (and in the 1980s there were proposals for a 9, 12, 15 and 23 story tower on the same lots). once over the hill, franklin leads down into bayside, where the bayside trail is currently under construction. it will feature pocket parks, a bridge over franklin arterial for pedestrians, nice lighting, and public art. it will also run between any new development in the neighborhood (which has all been postponed due to the economy) and link the boulevard with deering oaks.
This is a brief sampling of what has been going on. There are also plans to create a new gateway to Portland on the western side of the peninsula with the new veteran's memorial bridge, the new mercy hospital phase one and later phase two, maine medical center's new addition, etc etc etc. also some light rail has been considered, but these are all either minor projects that add up to significant projects or things which are just in the talk stages.
Sorry if this was more than you were looking for. I hesitate to talk too much on here unless I know someone is interested. And, this is me being BRIEF.