Hey there... just thought I'd add my two cents to the discussion: I am currently developing daily in Lasso. I was hired here (big New England university) about 1.5 years ago as a web programmer... with little programming experience (In a former life, I was a web designer. I knew CSS and HTML like the back of my hand, but only some very limited php). In fact, I hadn't even heard of the Lasso programming language before I started here. Anyway, they were pretty confident that I'd pick it up quickly. As skeptical as I was, they were right. The Lasso syntax is quick and easy to learn. Once you wrap your head around the syntax and the [SquareBrackets]
, the rest falls into place instantly. In a short time I was able to build some really complex, database driven, web apps.
As far as community, clearly Lasso's is nowhere near the size of that of php or ruby... but what I've found is that Lasso's developers are die hard fans of the language and thus are very active and helpful. Personally, I find a small devoted community more easily approachable and less intimidating. Most of the really juicy Lasso conversations take place on LassoTalk. Oh also, I went to the Lasso Developers Conference last year and was blown away by the dedication of the Lassosoft company and the developer community. (Not to mention all of the exciting stuff coming up in Lasso 9... later this year?)
Some downsides to Lasso: First and foremost, cost. It's expensive. There's no two ways about it (though if you're just looking to build something for demo or for a very small deployment, you might be able to get away with the developer's installation). Second, lack of mature hosting options. Take a look at the vast amount of stuff you can get in any random $5/mo. php hosting plan and compare that to anything you can find for Lasso. Yeah, it's pretty rough out there (these guys are not much to look at, but are pretty reliable: cheaplassohosting.com). I'd guess that most Lasso users are hosting their own solutions though.
If you decide to keep going with Lasso, here a few resources that I've found to be invaluable:
tagSwap - a puplic exchange for lasso custom tags
Lasso Reference
Tip of the Week
Also worth noting, there's a Lasso environment for Eclipse as well as a built-in support in Panic's Coda (which I enthusiastically endorse!).
Yeesh... didn't mean for this to be so lengthy. Anyway, I'd be happy to answer some specifics for you. Good luck with whatever direction you choose to go in!