You will be able to go a long way only with a tech-savvy person who can follow the instructions.
Essentially, you want a CRM (Customer Relationship Management Software) and there are plenty of them. Find one that looks ok, install it, play around and be ready to start over if it's not good.
Probably the only thing that could be "interesting" is the link to Google Drive, but I would expect to be able to add that pretty easily via a plugin or setting. Saving documents in Drive, Dropbox, etc. is hardly new.
What was there first … the chicken or the egg?
Do you choose your CRM and then find someone who can customize it? or do you find someone you trust and go with the CRM with which they have experience?
Are you getting someone to meet you who knows the intricacies of Canadian business? or go abroad where you get more for your money?
There is no real answer to that, and you may continue to talk in the discussion with your new technical person if you can prove that you have done some homework and know what you are doing and what is not on some of the known systems. For example, you really like zoho, but it's not self-hosted, or you do not like the UI on another, but how easy is it to add custom data.
How long it will take?
You do not know this until you have selected and identified your CRM does not do.
If it is just configured, it may take several hours. If it's a big job, it could take weeks.
You may have a grocery list of requirements and opt for "quick successes" to get started and invest in customizations if you're already up and running and proven that it's the right CRM for your business.
Oh, and the FWIW Doctors Records are also kept in the cloud.