For starters, the thing is architected poorly, so that does play a big factor in it. I know, I know, it's always the new guy inheriting an existing system that lays to claim that the inherited thing is a piece of garbage, but in this case it is undeniably true. And I can tell you, as someone who has been doing .NET consulting for the last 8+ years, it's not uncommon for MS based solutions to be architected this poorly, but I'll get to the reasoning behind that later.

So yes, poor architecture, lazy design choices (the wrong kind of lazy) but what is most aggravating are two other factors: cost and maintenance. Of course the very first thing I did when I settled in as the new CTO was to figure out how the thing was maintained and how much the thing was costing us a day to run. At my former CTO gig, massify.com, one of my proudest achievements was getting the daily cost of running the site below the price of a pack of cigarettes. Now we are talking about a user generated video content site with not exactly insignificant amounts of traffic and some very healthy storage requirements. When we started out, it was running us around $300 to $400 a day, but by the time I left, it was about $8 bucks give or take. And during the three years I was there, the site never came down unless we took it down for some kind of database migration or similar updating. And all of this happens thanks to OSS software and the ease of use of unix.

Now we are in a situation where we are paying for the server OS's, the SQL server instances and a variety of other utilities to keep things running. Not to mention the yearly MSDN subscriptions. That shit is expensive.

But what is worse is that it's such a pain in the ass to update and work on. Remote Desktop is retarded, but I have no choice as command line maintenance is simply gag inducing. Something that would take me mere minutes in a linux command line takes me an hour or more clicking around like an idiot in remote desktop. Good luck remotely admin'ing a windows server taking a massive CPU load. Now when I was at Massify, I could maintain and monitor our whole fleet of servers from my phone - and on a couple of occasions even did so while sitting through the previews at a movie theater. Do that on MS? MMM ... no.

But back to bad architecture and why it's endemic in the MS development world. ASP.NET. ASP.NET is such a convoluted, poorly conceived, poorly executed pile of shit. THIS IS COMING FROM SOMEONE THAT USED TO SING ITS PRAISES. And when ASP.NET is a cornerstone of .NET development, I don't think it's implausible to rationalize the rampant bad development practices of your typical MS developer back to it and other MS technologies similar to it (I'm looking at you Sharepoint). You see, MS is chock full of shitty architecture. And MS devs learn from MS. It's a cycle of shit that is constantly perpetuated by each release of some new MS technology. And I can tell you, I've seen it time and time again - working for companies like Pfizer, R/GA, some of the top 5 interactive ad agencies, etc. Finding a great MS developer is like finding a great PHP developer. They exist, but are such a minority as to be almost mythical. We used to joke that MCSD stood for Microsoft Certified Shitty Developer. Well, we always pitched it as a joke anyways, in case anyone ever overheard.

So, now we are currently wiping the slate clean and moving the whole thing to an OSS stack. And so far, even in the rough beta stages, we've already demonstrated how superior that whole ecosystem is to where it was before. It's very satisfying to show our licensing agents our new shiny search system (using a heavily modified Solr) and watching their eyes light up as we do things with it that the old MS based search engine simply could never do.

So that's my rant about that. MS is dying shit as far as I'm concerned, only used by people who are somehow locked into it, or are the bad kind of lazy and don't want to challenge themselves. I know that's not very objective, but it's the lessons I've learned.

PS. When I was interviewing with the company, I literally had a 4 hour conversation with the outgoing CTO about the benefits of MVC. He couldn't see them and I couldn't explain it to him in a way he understood. He kept pointing at ASP.NET user controls and how great they were. Of course, several months later I find a page on the admin site that is roughly 26K lines of code in the codebehind with a nice spaghetti mixture of HTML and SQL and C# code. I nearly quit when I saw it.

Do you have an idea why this is the case? Or the other way around why the architecture of OSS projects seems to be saner?

disclaimer: I have no exposure to the MS stack, with the exception of playing around with F# which in my opinion is a very well designed language.

At some point, MS probably realized that either these tools are not enough or their customers are asking for more because businesses are getting more complex and agility is required.

MS, known as the company that is great in terms of partnering and pleasing everybody except developers, decided to re-brand its offering to be more developer friendly. But at the same time, still serving the non-developers community as well (which seems to be dying slowly because well... if you don't like computers, you will not like it at all, period. You will hire someone to do the "dirty" job for you).

It'll take a while to transform the old MS to the new MS. If they ever made it.

Meanwhile, (some) OSS projects didn't have ambitious goals. They solve the authors's problems. During the inception of the project, they didn't care about the non-developer audiences. They care about themselves: developers.

I only catch glimpses of the MS world when I have to use common libraries originally developed by our Windows experts, whose design decisions often leave me puzzled. I am curious about what you think about the idea, that OSS culture incentivized creating architectures conforming to fashion trends, while MS culture incentivized to finish feature X until Y - no matter what it takes (just do it Scotty).

e.g. in the OSS world beginning of 2000 J2EE spawned heavily over-engineered solutions, which were displaced by the convention over configuration trend exploding (mostly due to Rails) around 2006. And now the TDD/BDD crowd are fighting it out with the Architecture & Patterns gang with the DDD and DSL tribes assimilating the surviving concepts...

A member of a currently hip fashion trend will have a better staying power in a nasty flamewar caused by a random design decision about the color of a bike shed in an OSS project than a lone warrior. So you start having design styles competing for followers.

Meanwhile in the MS world (wild guess following) heavily funded 'central planning solutions' (from frameworks to design styles taught for certification purposes) offered by MS stymied competition of alternative approaches. A focus on - if I understood your correctly - usually very risk adverse business needs, while keeping the actual code of produced solutions hidden from outsiders additionally put developers under pressure to avoid experiments.

Would it be reasonable to say that we have an evolutionary system of small actors competing for developers interests (OSS) fueled by <insert book about OSS phenomenon> vs. a central planning approach of a major corporation backed by a huge war chest?

The search engine is a customized version of Solr.

The front facing website is done in PHP using a framework we developed at Massify (http://heavyfuckingmetal.com/). We thought about going the ruby or django route, but the front end is so light functionally we decided to go with what we knew inside and out. We'll also be using MongoDB for certain things.

The way we are phasing the rebuild, the SQL Server is the last thing we're migrating, so that will stay in the mix for awhile. It's the most complicated piece because it has a bazillion stored procs that need to be migrated/refactored out. The structure is fine for the most part, though a little de-normalization is probably in order. Eventually I hope to have that running on PostgreSQL by next winter.

The backend, or admin, will be done with heavymetal and cappuccino for the front-end.

As an aside, the entire rest of the company is mac based, so we've written a couple of desktop apps, as well as some server apps, in objective-c/cocoa using quite a bit of open source libs. We'll be putting some of our own code public on github in the next few weeks. We've also done an iPad app for showing our image portfolio to clients.