Point me in the right direction, Programs / Info / direction.

It's interesting. To do standard reporting stuff is pretty cheap and trivial. Word processing, web and e-mail are all available in good quality open-source (free) software. So, that saves you the cost of a "productivity package" (about £180 per seat) before you start.

Next, your drawing tool. I think to do effective design work you need to be looking at 3D CAD. Yes, It's lovely to draw in pencil and paper, but there is a time and a place to do it, and 2D CAD does not progress far from this. Cost for 3D CAD starts very cheap, and ends at a greater license fee than the annual turnover of a small country. I like Rhino, it is very powerful, and cheap enough for the small business to buy without worrying.

Your analysis is slightly more of a problem. The first question is what sort of analysis?

Stability
Powering (Resistance, propulsion and sail theory)
Wave-making
Dynamics or maneuvering
Refinement of lifting surfaces and vessel balance

The prices for software to handle these problems rise roughly in the order they are listed. You need to think about the operations you do now (which I guess is lines-plan and stability, with limited resistance and propulsion) and match your first round of software and hardware to automate this. The price you pay will be entirely dependent on which package(s) your users feel is most appropriate.

Everyone has preferred pieces of software, and systems to work on. I personally use Linux for (software and electronics) development and documentation, and run (only) Rhino4 on Windows. This requires two systems (or one system dual booted), but with tools like synergy for keyboard/mouse/clipboard sharing it makes a lot of sense. However, If you don't need to do development work, you may find a single PC is adequate.

A plea, though. Please talk to a local systems administrator (by which I do not mean a support monkey) before you install any system. You'll find plenty lurking around Linux User Groups. These groups tend to be filled with skilled users, some of whom will work as sysadmins. In the nature of the open-source community, most will give advice freely, but you will need to give them some compensation if you wish to employ them to do a system setup for you. Here is a useful list of groups: http://linux.org.au/foss_in_australia/LUGS/NSW

As I see it you will need a sever with plenty (a few terabytes) of expandable disk space (probably in RAID 5), and a workstation for each employee. You need a plan for nightly or weekly (possibly rotated) backups and recovery thereof, and if you can (and it's pretty easy to do) a secure off-site backup. You will also need to consider the standard domain services (login, home directories etc.). You may also wish to think about a version control system. You may also wish to run an internal web-site with a wiki, or similar collaborative tool to allow users to store useful information. We do this at work, and once you get into the thinking it works really well. You may also want to run an e-mail domain and external web server. Whether or not you do this in-house will depend on the people you have and the quality of your internet connection.

These days hardware is pretty cheap. However, if you're starting from scratch you'll need quite a lot of it. Server software is free if you go the Linux route, but then you'll have to retain a friendly Linux admin. This is likely cheaper than paying an MS license and an MS admin (who, experience has shown, likely won't be half as good). The cost in all modern systems is largely software, so pick your hardware wisely, and the software that runs on it more-so. There will be a learning curve, but you have a unique scenario, where you have no prior investment.

The two most important things to remember are:
1) Ensure your users have a fast and stable desktop system which does what they need it to do.
2) Paying large amounts of money for anything does not make it inherently more suitable for the task.

Hope some of this helps,

Tim B.