Help this guy: saas, cloud, the whole shebang

During the week I received an email from a colleague who runs a tiny lawyering business. In many ways his challenges are no different to those of the large enterprise. Right now it is difficult to suggest a really simple solution that meets all his needs but it should be possible to get to 80%. I have some ideas here. But I want to know what you think. In this day and age and with the tsunami of innovation we see coming at us, it cannot be beyond the wit of smart people to come up with something workable - at least in the interim. With his permission, I reproduce below the substance of the email. Feel free to go at it.

I have the ubiquitous Small Business Server, and a BES to drive two Blackberries. The SBS needs rebooting almost weekly due to the critical security updates that Microsoft throws at it. Drives me nuts. Servers are supposed to run for hundreds of days at a time, aren't they? I

have this notion that law firms are nothing special, even though the Bar thinks of itself as some sort of God-appointed group of Protectors Of The Universe. BS. We're consultants. And as such any decent software that would run a consulting firm will run a law firm.

The only difference with law firms is this business-necessity thing of keeping far more rigorous records than the average social media cream puff shop. Filing. Records management. Document management. Etc.

The end state I am aiming at is that I can work out of my phone and my brain. I want to push everything into the atmosphere and access it through a browser. I'm sanguine about the current reality of this. I'm not going to bet the farm even on Zoho or Google. But that's where I'm headed. And I need someone to help me get there.

My dim understanding and desire leads me to guess at the following: - a project management or customer relationship or whatever you want to call it software that is document-centric. The effort to put a document into the system must be trivial. In other words, the cost of putting a document (email mostly, but Word files, etc. as well) must be less than the cost of leaving it out. "Cost" means human effort. - accounting/financial system for now is Quickbooks on our server, but I'll migrate to Quickbooks Online by year-end. Or something equally simple. Once you go to fixed pricing your life becomes a lot easier. And finding people qualified to do Quickbooks work is easy and cheap.

It has to talk to our Blackberries. For the moment this means push contacts, calendars, and email. We'll carry laptops for the rest of the stuff. To give you an example of where we are heading, we are two lawyers. My young associate is posted in NY for a month on a client project. We need to make that lifestyle work.

I plan to start spending big chunks of time in Saudi Arabia to do marketing and work with clients. Part of my problem is I don't even know the questions to ask but then I don't want to be the expert.

The phone system needs help, obviously. We will add more lawyers. Probably another one in 12 months or so. We'll grow to perhaps 6 - 8. So really the idea is to take us from the standard "I gotta rack of machines with nice blinky lights so why the heck does it cost me so much and why do they die all the time?" business to as little ownership of software/hardware as possible.

The best analogy I can think of is this small time consultant named Ross Kodner. He says a paperless office is a myth, but a paper LESS office (meaning less paper) is a reality. Pure cloud worship for a business is a myth, at least now. But it's getting there and if I can take advantage then I will.