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OP here, back after some deliberation.
I decided to make a chart of a 5 year plan of gear purchases. The budget line starts at $6k as discussed and its slope represents $770 of film and processing per year. The film body is the EOS 3 and the digital body is the EOS RP with an EF-RF adapter.
The following lenses are selected for a high level of image and build quality, with a large focus range without large gaps or redundancies. They all have a 77 mm filter thread.
1. Canon EF 16-35/4 L IS USM
2. Canon EF 100-400/4.5-5.6L IS II USM
3. Sigma 50/1.4 DG HSM Art
Not accounted for are knickknacks like filters or a tripod.
The film-first approach breaks the budget due to three year's worth of film and processing, which is could be put towards a pretty high end digital body instead.
Digital-first works because there are no film or processing costs the first three years. All the skills for film can be practiced with digital at a much lower cost.
Other ways to meet the budget is to swap the tele zoom for an entry-level or shorter range alternative, or delete the 50/1.4 since it's the least versatile, many photographers I've seen like to either shoot wide or long and not much in-between.
The final way is to stick with just a single medium, represented by the dotted lines. Digital has the obvious advantage of not needing a film or processing budget.
