Comment What skillset do you have? (Score 3, Informative) 227
Since you want to be the IT admin guy off the side of your desk, the short answer is - can you manage it on a NAS? If not then stick with what you know and focus on your day job - the first time you have to spend 2 days fixing or configuring something that's new you'll have blown any cost savings from getting a server anyway.
I run what you're describing, though I let the router handle VPN access. If you stick with Windows Server, everything you want to try and do will have a solution you can find in 2 mins on Google, if you go onto a proprietary NAS you will end up working around a lot of things to get them how you need them - Offline files for your users will be a little bit cranky, how you do backups will be limited to the NAS' interface, if you want your security settings 'just-so' (presumably important in your industry) you'll need to make sure the NAS software can cope with that.