First of all, all ADs are different, and Rolex rules for each AD can be different, there is no right answer.
In my experience, do my Rolex purchases put me to a more favourable position for the next Rolex? Certainly not. The attitude is, by selling you Rolex watches, AD is doing you a favour, selling you an item below market value, handing you cash in their mindset. In return, they expect regular purchase of items that have fat margins.
But I guess if you and your family shopped that 10+ Rolex spread across the last 20 years, it proves you to be a regular buyer and could help.
At the end of the day, it's all about money. If an AD aim short, it sells the Rolex directly to grey market dealer, pocket extra cash instantly. ADs that play the long game? They use their Rolex to build relationships with high value clients. Question is, what's your position in this Rolex game?
My sincere advice, never spend extra on other items in the hope to get your Rolex, it won't work, not until you spend an obscene amount, not worth it. Just be patient for the market to cool down, or go grey.