What are your experiences with the Mac App Store in a small business?

Combine 2 and 4. No way will some employees have the extra $60 to spend on software at the exact moment you need them to have it. So use their existing AppleIDs if they're already using them on that machine, and charge it to the company card. If they don't, then use their employee emails to make new AppleIDs. OR require that employees create new AppleIDs with their work email addresses.

Refresh! Someone said the same while I was writing! I have done #2 before for a small 5 person or so setup. They were an outlier in their company as a Mac using group so their corporate email and their company issued cards as high level sales folk was available to use in that fashion. I read Apple's site and I see what you mean about the DUNS thing... That does not make it possible for you to merely buy in volume for all in one set. However they also seem to be working off a personal ownership sort of deployment model in their business guides, so I think a combo of 2 and 4 would make sense. They have their own company mail accounts. Check. They have personal Apple ID. Check. A Company credit card(s) exists. Check. Employees have the ability to make expense reports to company. Check. If so, then the paid Apps are purchased with their Store account on their company email with company card. Then they switch to their own personal account they can get their own free apps if they like... Though honestly they could do that on the company account as well. If the employee later needs to get a paid app for company use and mistakenly uses their own account for it. Then they must fill out the expense report to be reimbursed.

Just some clarifications as situations vary between companies, and even within particular companies as for example there are some people with personal Apple IDs in use on the work computer and some people without. Often the company card would just be the owners AmEx used multiple times. From what I understand that isn't a problem, but maybe there is some limit that gets it flagged for fraud from the credit card company or from Apple. I could certainly keep track of this info (for example with option 3) as I have a secure database set up. My concern is that it isn't worth them paying for me to do all that organizational legwork as the cost to just repurchase the software when an employee leaves wouldn't add up to a sizable amount. Likely purchases are the OS, BusyCal, Pixelmator, and Numbers so it shouldn't add up to a lot—maybe $30-100 per person tops. If Filemaker, Office or other more expensive software goes Mac App Store only then it would be be a different game as that would be upwards of $500 per employee, but I don't see that happening so this should be just Mac App Store only software. Anecdotes about specific methods that led to confusion from employees or worked smoothly would be helpful.

I'd combine 2 and 4, and two accounts on the box. "Installer" and the user. The Installer account gets the corporate Apple ID setup in iTunes/App Store. The user account gets, if the user wishes, a personal account, but I'd honestly discourage that, under "a work computer is not YOUR computer, why are you trusting YOUR information on it?" But that's me. Also, if policy is that only designated people can install software, you give them the password to the installer account. There is a training issue of "flip to this account to install software." If they don't setup iTunes in their personal account, this is much easier. If there's more that a few people and a network, central auth starts to become useful, but at that point, you're pobably big enough to have a DUNs and need 20 copies.

Have you looked into using http://www.apple.com/business/vpp/? It can be used to redeem Apps on OSX clients and maintains its own internal database (spreadsheet). Using this method, each client can still use their own Apple ID, but all purchasing is done through the centralized Program Facilitator account. The caveat is that AFAIK, Apple Configurator (the goto program from deploying iTunes apps to iOS devices) doesn't really work with OSX as an end client. You'd need to e-mail links to end-users or post them internally.

Have you looked into using Apple's VPP Program? This is my option 1 above, which has the drawback of a minimum purchase of 20 copies for each piece of software.

Missed that, sorry. Working in education, 20 licenses is only a barrier for bulk discounts- we can purchase as few as we want at full price. Didn't know that was a hard barrier for the business VPP program. Lame.

Missed that, sorry. Working in education, 20 licenses is only a barrier for bulk discounts- we can purchase as few as we want at full price. Didn't know that was a hard barrier for the business VPP program. Lame. Is there a different program for education? One of my clients with around 20 users is a school, and purchases might be intended for just the admin people and not teachers for example so I wouldn't necessarily want 20 of something, and I also don't want to manage 20 AppleIDs of course.

My small company does 4ish. Employees set up their own AppleIDs; most people (including me) made new ones just for work (see below). We use our own credit cards. We get reimbursed promptly, so it works out ok. I've never used my personal account by mistake -- we need (informal) prior authorization to buy new software, so that puts me in the mindset to use my work account. Also, we're not buying software everyday. The reason I set up a new account is because I have a mac at home that I purchased some software for, and if I use the same account and software at work, then I can't repurchase the software; I just get prompted to download the already purchased app. The reverse is also true (installing the software bought for the work computer at home). It's not a huge deal. But this can be kind of sticky if you want to follow the http://www.apple.com/legal/itunes/us/terms.html#APPS very exactly.