Aotearoa / New Zealand

Move your email to 365 if you’re doing licensing there already. You’ll be able to make shared mailboxes to your hearts content. This may be a minor increase to your existing licensing with Microsoft but probably worth it. You’ll offset the cost by dropping your current hosting provider and maybe even get some more Microsoft features while you’re at it.

I’d recommend not putting any servers on site if you don’t have them already. Especially if you’re already using overdrive and Sharepoint. If you need something like a more traditional file share look into azure files.

Servers mean maintenance, security, availability and life cycle management. You’re in a position where nothing to migrate means going straight cloud. Microsoft can provide everything you need and the cost may seem high but it’s worth not having the on premises headache.

As much as I hate it as a self-hosting enthusiast, I probably have to agree with @[email protected]. Unless you're willing to spend some time (not a lot) on maintenance regularly (this is the important bit) - it's going to backfire. Cloud is easier.

Having said that, this is the perfect time to establish the foundational attitude towards IT solutions at the company. Cloud is good for massive scaling, but it's an absolute ripoff at running something all the time. Proprietary vendor lock-in is a pain that inevitably rears its ugly behind at the worst possible moment. So:

• Nextcloud - file sharing, calendar, contacts. Also a ton of other stuff, but we don't care about it now.
• Postfix+opendkim+opendmarc+spamassassin+postfwd+dovecot is the email solution I use. Sounds daunting, but I found it to be the easiest to maintain as all the moving parts are small individually. I avoid "all-in-one" solutions as they always manage to cock things up during upgrades. I'm also running this on a rolling distro so I never ever have to go through the utter bollocks that's a major version upgrade.
• OpenLDAP - I'm only looking into setting this one up for myself, and it's an absolute overkill for a company that has 5 users; pretty much everything integrates with it, though.

Unless you're in a position to scale up majorly in the near future, and need systems in place for a hundred employees, don't overthink it. Get yourself a second NAS for all of your critical data, and keep it airgapped from the rest of the network except for your weekly backups.

I'd look into using google for your email and calendar service also, as it has good integration between email and calendars, plus you can share calendars between people.

So, this is what I do for a living. I work in Enterprise land these days (thousands of users and servers), but I spent a lot of time in SME and non-profit land also.

There are three main paths:

1. Self hosted
2. Microsoft
3. Google

Self hosted looks like the cheapest one, but unless you have a person actually doing regular IT, it's the most expensive. One phishing attack and your files are encrypted/held to ransom. Without IT being there to restore from your regular backups, you are dead in the water. I would not recommend this path if your intent is to set-and-forget.

Microsoft is the benchmark. Everyone knows Office and Outlook, the product is mature and integrates perfectly into Windows, the most popular OS.

Google's product does pretty much the same stuff, and is easier to manage for a middling IT user. It does some things a bit differently to Microsoft though, and your users may hate the Google browser-based office apps. If they can adapt though, id normally recommend Google for a small business.

Both these will allow you to centrally manage users and files. Both will handle restoring files from backup with no maintenance work from you. Both have video conferencing and calendar/email sharing. Both will let you use your own domain.

Regardless of which you select, I recommend having an MSP on retainer for IT stuff. Just knowing you have IT experts a phone call away is as valuable as insurance. Some of them are cheap to retain and charge by the hour.

I know my rate was 🇦🇺$150/hour when I worked with small businesses 8-10 years ago. No idea what today's NZ rate is, but that hopefully gives you a ballpark.

I don't really have anything else to add that hasn't already been said, so I will just leave you with the route I ended up taking.

I decided upon Google Workspace. The price vs convenience is very high, and I personally have no problems using either Microsoft or Google office software. Google admin is easy for users, and you can easily set up aliases which point to different email addresses. For example, sales@ and info@ can all point to axisential@, and it handles return email addresses as well. I don't know how MS handles this, as I don't have much experience with their enterprise side.

Instead of self-hosting a website, storage, etc, for many of the reasons outlined elsewhere in the comments, I went with Google for file storage and Shopify for the web-store. The cost you pay is more than made up for the fewer man-hours of running a system yourself, and the security built in to the platforms. I have experience with Magento, and I will never use it again.