Request for Comment - late 2008 MacBook as starter Mac I am refreshing my home technology stack and considering a Mac. I could use some advice about new versus used.

I am currently running a hodgepodge of old 2005-era machines running iTunes, web sites, dev, etc, all Windows/Ubuntu. Want to reduce that footprint and maybe start learning Mac.

A Mac seller in my hometown is offering a MacBook from 2008 for $399 with the following specs:


Late 2008 model, 2.1 GHz Intel Core 2 Duo, 13.3-inch glossy
widescreen display
2.0 GB RAM (upgradable to 4 GB), 120 GB hard drive
Mac OS 10.6 Snow Leopard installed
Comes with iPhoto, iMovie, Garageband, iTunes, iChat, Photo Booth and the Safari web browser


Based on those specs I believe this is a MacBook 4.1.

I'm looking for something which would support the following roles:


Convert programs recorded on Tivo to iPhone/iPad format for transfer to devices;
Watch iTunes movies on TV (could connect directly to TV); 
Experiment with XCode development - would like to learn iPhone app development;
Host an Apache/Tomcat type stack for internal development.


My questions:


Right now price is more important than portability. How much future-proofing would I buy with a new Mac Mini for another $200? I am just looking to learn about Mac, I don't use it for work so not keen to drop a lot of money here without some experience. Not interested in the Craigslist route.
I know newer Macs are more user-maintainable but it seems like a lot of that changed during 2008. Can I upgrade this model's internal components myself, esp. the RAM? Have done lots of upgrades on PC cases, new motherboards, CPU/Fan, power supply but Mac is new to me and not sure about this model. 
What is the software support picture like for the apps I've listed under Snow Leopard? Will I have to upgrade to Lion for XCode, iTunes updates, etc?
From your description, this is a MacBook4,1 or MacBook4,2. They both have the same compatibility, and are essentially the same machine for considering the future:


That MacBook will run Lion once the RAM is upgraded. It will not run Mountain Lion. Today's Mac mini would. The MacBook4,1 and 4,2 have less than a month before it becomes unsupported by the next OS. The Mac Mini probably has several years.
Macs are not generally user maintainable. (Edit: To be clear, I mean to the degree that you're used to.) The RAM in that model is user upgradable. I believe it's just three screws in the battery compartment.
You will need Lion for the current version of Xcode. In a month or two, you'll probably need Mountain Lion for the latest Xcode. Apple may ship the next Xcode with compatibility with Lion (say, 40% odds), but certainly next+1 won't be compatible.


Sources:


OS X Mountain Lion (Wikipedia)
MacBook Model Specifications (Wikipedia)