Customize automated emails (based on integration with existing booking reservation system)

Hello, I run a walking tour website built on wordpress ([login to view URL]), and use [login to view URL] as my booking reservation system. It's a well-developed booking system and it allows me, among others, to automatically trigger many types of emails to customers when they reserve a tour, send a post-tour thank you email, etc. However, the level of customization for emails is lacking as they only offer a few email variables (such as name of tour, customer name, etc), and I cannot set the time when the emails are triggered. Checkfront does have an API, which allows further customization (more info here: [login to view URL]). The emails I would like to be able to send are(and I note that I can do this in checkfront currently): 1, a thank you for reserving with us email; 2. a your tour is now confirmed email (which would have to be triggered when 3 or more customers have booked the same tour – note: this is not currently possible automatically in checkfront, and I have to do it manually; I would like this automated by you); 3. a your tour is tomorrow reminder email; 4. a thank you for coming on a tour email. Beyond that, I would also like to customize and trigger emails to our tour guides, which does not happen currently in checkfront. For this, I want to send 3 emails: 1. an email to our guides, letting them know how many people are coming on a tour, and their contact information (this info is currently collected by checkfront during checkout). This email would be sent to our guides 24 hours before a tour runs. 2. an email sent to our guides confirming the tour will run, triggered when the number of customers reaches 3 for a future booking. Lastly, 3. an email sent to guides 24 hours before a tour runs, telling them the tour will not run, if the numbers of bookings has not yet reached 3 bookings by then. In terms of email variables, I would like to customize, for each of our tours, the following: 1. the start and end points (meeting place address, photo of it, and link to map to it); 2. name of tour guide + their photo + twitter handle; 3. phone number for guides in terms of emergencies; 4. name of restaurant/eating place post-tour and photo or logo for each of the tours; 5. line about recommending a snack depending on when tour runs (i.e. if run during supper time, so people know to eat in advance) + recommendations for places nearby starting place where people can eat; 6. a short tour description; 7. integration of current weather forecast for the day of the tour; 8. links to the 'further reading' folders for each; the distance, accessibility and duration of each tour (so in total, about 20 variables). I am flexible on what you choose to use to build these emails in: either build on checkfront existing system based on their api, or use an existing wordpress plugin automatic email, or you build a custom wordpress plugin just for this. Lastly, I want the emails to look aesthetically pleasing and have the same look/feel as our website. Their should include our logo, similar font as the logo and website fonts and colors, and they should contain our contact info such as our twitter handle, website, phone number, etc. (customized header and footer, basically), sent in both html and text version. I have created the exact text to be used for each of the emails and for each of the variables for the four tours we currently run. I would want something built in such a way as to easily allow us to customize future such emails for any future tour we will wish to create and run. I would want you to start this right away, and finish the project in max 4 days. When bidding, please do not submit your copy/paste portfolio with your work - I much rather have a few words from you to let me know that you are human and have read exactly what I would like to do. Please also tell me how you would do this (in checkfront, or build your own wp plugin, etc. – this would be helpful info). Thanks.