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Technology is moving rapidly. Hewlett Packard and Dell have started pulling consumer based hardware (in-office servers) off the market. In the same way Microsoft is no longer servicing Windows 7 past January 2020.
In-office servers will eventually suffer the same fate. Moving to the cloud is no longer a question of "if" but "when".
It's impossible to make an informed decision if one doesn't understand the intricacies of technology evolution. The technologies that served dentists in the 90's and early 2000's are rapidly aging out, and the few solutions left in the market have a similar infrastructure to in-office servers.
Which could leave some dentist investing in a short term solutions for a long term problem.
To begin one must understand the subtle, yet importance of single vs multi-tenancy computing.
A community of houses vs a community of sky-rise condos. Everyone still has a key but each floor is highly customizable.
Just because something is cloud hosted doesn't mean it is cloud based.