To Create lead management and email marketing system

I am looking to connect all the dots into one meaningful and automated lead management and email marketing systems. Here's the breakdown, I hope you will understand :-)

a) I am developing a couple of pop-ups for my web site using OptinMonster: free e-book and discount vouchers.
b) I have a couple of free lead magnets listed above and small tripwire offers (studio loops for $9) already prepared.
c) I have Gravity Contact forms on my website.
d) I also have a MailChimp account and Hubspot account.

What I am looking for is to connect these elements into a functional lead management and email marketing system (btw, HubSpot I don't really care about, it can be replaced with another CRM tool).

There are basically 3 scenarios that i am looking to implement ASAP and one extension further down the line (option 1a below):

1. Visitors land on site, pop-up comes up, they sign up successfully for our free e-book or gift voucher. Pop-up closes, visitors get an automatic email sent to his email address with welcome message and download link for the e-book or voucher. Customer's email address is entered into our MailChimp list and CRM tool automatically. After that customer goes into regular email marketing system.

(1a. Further down the line, I would like to extend this funnel so that when customer clicks on url from the email and downloads free e-book, he/she gets a new screen with a small-value tripwire offer (studio loops). I have copy, visual and programmer to prepare the page already). After that customer goes into regular email marketing system.

2. Visitors land on site, they like what they hear and they go to our contact form and send a request for a free quote. Their email address is immediately added to our CRM tool and MailChimp contact base. After that they go into regular email marketing system.

3. Create effective emails for the existing customer base in MailChimp with download link in the email for whatever we are promoting.

Please let me know if this is something that you think you could do and what is your estimate of the cost? Having references that can be experienced/tried is definitely a plus.

I look forward to hearing from you.

The website is https://www.supremetracks.com/