Are Cloud Services Right for Your Business? A Decision Guide for Maine Small Businesses

Short answer: for most Maine small businesses, email, calendars, documents and the common line-of-business apps belong in the cloud (Microsoft 365 or Google Workspace plus a cloud server where needed), and the on-premises server can be retired at its next replacement date. The exceptions are real: firms that work with very large files (engineering, architecture, video), offices with slow or unreliable internet, and businesses running legacy software that only works on a local Windows server. Moving to the cloud changes where your data lives. It does not remove the need for backups, security settings or someone to support it.

First published in 2019, rewritten October 2026. The questions are the same; the answers moved, because Microsoft 365, SharePoint and cloud servers are now the default for new businesses and fiber reaches most of Greater Portland.

What does “the cloud” mean for a small business?

Three different things, usually mixed:

1. Cloud productivity: Microsoft 365 or Google Workspace for email, calendars, chat, and documents stored in OneDrive/SharePoint or Google Drive. Nearly every small business should be here already.
2. Cloud applications: accounting, CRM, practice management, point-of-sale delivered as a subscription in a browser. The vendor runs the server.
3. Cloud servers: a Windows or Linux server rented from Microsoft Azure, Amazon or a hosting provider, for the application that still needs one. You still administer it; you no longer own the hardware.

Will cloud services work for us? The questions to answer first

• How big are your working files, and how fast is your internet? A 2 GB drawing opened over a 50 Mbps connection is a coffee break.
• Which applications do you depend on, and does each have a hosted version your vendor supports?
• Who needs access from where? Remote and field staff are the strongest argument for cloud.
• What compliance rules apply? HIPAA, CMMC, financial regulators, and insurers all have views on where data may live.
• What happens to the old data? Migrate everything, or freeze the archive locally and start clean?

The engineering-firm example from the original 2019 post still holds: when drawings and their companion files are not stored locally, working from cloud storage is too slow. Those firms keep a local file server (or a local cache appliance) and put everything else in the cloud.

What does the cloud cost compared to a server?

A small business server costs roughly $5,000 to $10,000 every five years plus backup, power, warranty and the labour to maintain it. Microsoft 365 Business Standard or Premium runs per user per month; a cloud server for one legacy application runs a few hundred dollars a month. For a 10-person office without large-file needs, the cloud is usually cheaper and always more predictable. For 50 people with heavy on-site workloads it can go either way, which is why we run the numbers rather than assume. How to budget for either.

What does the cloud not do for you?

• Backups. Microsoft keeps deleted files for 93 days and deleted mail for as little as 14. Microsoft 365 is not a backup. You still need one.
• Security settings. MFA, conditional access, sharing restrictions and audit logging are off or loose by default. Someone has to turn them on.
• Devices. Laptops, printers, firewall and Wi-Fi still exist and still need patching, encryption and replacement.
• Support. The cloud provider supports its service, not your staff. “My SharePoint sync is broken” is still your problem.

How does a migration go?

1. Assess: inventory data, applications, users and internet; decide what moves, what stays, what gets archived.
2. Prepare: set up the tenant correctly (MFA, security defaults, retention, sharing rules) before any data lands in it.
3. Migrate: email first (usually over a weekend), then files into an agreed SharePoint structure, then applications one at a time.
4. Organise: a SharePoint library per team or function, permissions by group, a naming rule everyone knows. Dumping the old server’s folder tree into one library is how cloud migrations fail.
5. Back up and monitor: third-party Microsoft 365 backup on from day one; monitoring on the remaining devices.
6. Retire: wipe and dispose of the old server (properly).

Frequently asked questions

Is the cloud more secure than our server?

Microsoft’s data centers are more secure than your closet. Your tenant is only as secure as its settings, which is where most cloud breaches happen (a mailbox without MFA, a file link shared with “anyone”).

Can we move QuickBooks to the cloud?

QuickBooks Online is the cloud version; QuickBooks Desktop can be hosted on a cloud server. Which is right depends on the features your bookkeeper uses. Some desktop-only features do not exist online.

How long does a migration take?

Email over a weekend. Files one to two weeks depending on volume. Applications vary by vendor. A 10-person office is typically fully moved in a month.

What if the internet goes down?

Then cloud services are unreachable, which is why a cellular failover on the firewall is part of every cloud-first design we build.

Cite this page: “Are Cloud Services Right for Your Business? A Decision Guide for Maine Small Businesses”, Information Systems of Maine, Portland, ME, updated October 2026.

Want the assessment done for your office? Request a free evaluation or call 207-653-4143. Cloud migrations are part of technology consulting and ongoing support is part of managed IT.

Rick Lorello Founder

Rick Lorello founded Information Systems of Maine to give small businesses in the Portland area dependable, local IT support. Before ISM he worked at Spinglass and the Portland Water District and spent 10 years at TD Insurance. He holds a BS from Husson University and an MS from the Florida Institute of Technology.

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