Bike Rental Manager Ideas

We have many families who go on holiday together, but where everyone arrives at a different time. E.g. 2 bikes from 01 - 10 August / 2 bikes from 03 - 09 August and one of them with a child seat from 5 - 10 August / 1 bike from 5 - 10 August ... etc. Currently you have to make a booking for each date and extras cannot be selected for other dates, such as for the rented bike. We had the option of choosing a date for each product or extra with Checkfront and it was much easier to handle these bookings as they are normally all paid together.