Process checklist in CRM

We've created a new sales process that I'm mapping into the CRM - issue I have is that some of the tasks / milestones I would like to capture require very simple tick box responses but there are quite a few under a variety of sub categories so I don't want to create new fields for each one as I will run out of custom fields! For example, one subset of checkpoints might be: Gathering lead information - 1. Size of company 2. Number of vehicles in fleet 3. Current arrangements for fleet management 4. Health of company. Each of these steps (1 - 4) should be checked off (and preferably commented on) with checklist remaining visible in Lead record and carrying across to Customer / Sales Prospect record when converted. Any ideas?

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