Thinking of getting Salesforce - Small Business Owner. Enhancing existing client relationships

Hello Salesforce subreddit

I'm sorry in advance for my ignorance.

I'm a Financial Planner in Canada (small business owner) and my client investments and client personal info housed by my dealer have just been made available to be shared via API to Salesforce. I use a basic data storage CRM that I dislike, and I'm considering Salesforce as an alternative.

We currently use: Office 365, Mailchimp, and Equisoft CRM.

The extent of my knowledge: I've used a custom iteration of Salesforce enterprise for almost a decade as an end user (in my previous role). I was involved in a workflow project where I gave efficiency ideas to the company's Salesforce admin and they handled implementation. Now being the boss that's my task!

Here are some of the issues I hope Salesforce solves:

1) Follow up. If I send EXISTING clients an e-mail I need a response to, the ability to automate a simple e-mail reminder that includes an attached PDF document to the client that goes out periodically until I hear back from them. If the client responds I would like for Salesforce to turm off the reminders automatically. Or perhaps there's a good app that can work as a Salesforce addon that accomplishes this?

2) Milestone updates. When the client's investment values hit a certain threshold, a 1-time e-mail goes to them.

3) Automated birthday emails from my team

4) A checkmark task list post-client meeting we send of things we're working on, and things the client needs to do/work on, tied to their Salesforce profile. Something that if the client completes the task and interacts with the task list, it automatically sends the update back to us. Again, perhaps there's good app or addon that can accomplish this.

I wonder how hard it is to implement the above? Is it simply creating custom workflows and ap integration that a Salesforce rep can help with?

Or maybe it's better to hire someone for implementation ...

Thanks for your input