I find myself in the opposite boat, I have made commercial websites with Django and now find myself learning ASP.NET. My recommendation comes with the following caveats... regardless of direction the learning will happen. Django is a very battery included framework, so the initial process will be painless, I found that documentation and support for more advanced use cases to be fairly easy to get support.
I personally found Django pretty nice to work with.
I starting using MongoDB because it was much easier to implement in production then hosted SQL, and found that a lot of the limitation you think of from a document store vs a relational database were overcome by connecting the application to a graphql API, making retrieval seamless. Mongos latest upgrades as well as Stitch and Mongo mobile make it a perfect fit especially if your application will be cross platform web and mobile.
By streaming data from Dynamodb Elasticsearch provides the dynamic lookups for listings by activity, date, cost, ect. ect, providing a superior enduser experience. Amazon Elasticsearch Service
AWS Connect provides the voice to Lex text bot interface that runs through the data entry for a listing. The simple interface allows the logic for connecting AWS lambda functions that trigger the bot interactions as well as the data store in Dynamodb. Amazon Connect
Easy to utilize built in libraries for Alexa-sdk as well as ask-sdk and aws-sdk for integrating all the various cloud services and trigger lambdas JavaScript
