Anyone know if the wizards are at least present in Windows Server 2008 R2 Foundation? I bet they'd be handy for my dad...

If you are using Amazon cloud for your dad's medical data, then you should check carefully its compliance with HIPAA - last time I checked there were still some reservations about the compliance...

My problem with those wizards is that they essentially force you into setting up more than you actually need to have and actually increase the overhead for many simple tasks. I'm not opposed to wizards on principle, just those that SBS adds based on Microsoft's version of what they think is actually helpful to a small business. They require extra services to be running that reduce system performance and actually make things worse. I truly believe that MS could have built just as functional wizards but without that overhead.

But, like I said above, that only matters if you understand the differences. If not then no big deal as you didn't know the difference anyways.

No idea if the wizards are in Foundations.

The JungleDisk FAQ says JD can be HIPAA compliant if configured properly. I'm no attorney and no HIPAA expert, but I am smarter than the average bear with regard to IT and security. I use strong passwords and supply my own encryption key for the JungleDisk disk that the server backs up to. Not sure how else to make it more secure...

I'll let you know if I come across them. Server comes in a couple weeks. They'd probably be handy for my dad, though I would probably just use mmc for my management needs.

You're nowhere near the minimum number of units necessary in order to do the 3 year contracts which are like a rental of sort.

I think you guys are confusing what is and what is not software rental in Microsoft licensing terms.

Microsoft offers 3 volume licensing programs: Open, Select, and EA. With any of these programs, you can annualize your payments over a 3 year term. You can get into an Open agreement with as little as 5 units. These are perpetual licenses, meaning you own them outright at the end of the 3 year term, whether or not you choose to renew the agreement. You paid for the licenses, they are yours.

You also have the option of adding Software Assurance (SA) to Open and Select license agreements (SA is included by default in EA's). Think of SA as maintenance; If you have SA on a product and a new version of that product is released during your term, than you get rights to the new version. (SA has additional benefits such as training vouchers, packaged services, home use rights, etc, but that's besides the point of this discussion). Again - at the end of the 3 year term, SA will expire if you don't renew, but you still own the licenses outright.

Having said all of that, there is a special program called EA Subscription where the licenses do expire at the end of the term, but these are very rare. There are very few of these in existence worldwide relative to the other programs.

I was referring to none of those licensing options in my "rental" references. The Service Provider Licensing Agreement (SPLA) allows authorized integrators (of which I am one) to rent MS software to customers on a monthly basis. The cost is generally about 1/36th of the shrink-wrap+SA price each month. There are a number of circumstances, however, where the per-month licensing can be a very good deal depending on the infrastructure requirements.

The systems and licenses must be managed by the service provider but that is generally not too hard to accomplish, even in a situation such as the one described by the OP.

The vast majority (all?) of my customers do EAs or their industry equivelant so I'd reconsider how rare they are...

EA's are not rare. EA Subscriptions are.

Excellent call out, I failed to mention SPLA's.