The strategy can work for a while but it is not a sustainable long-term business model. It's more of a fantasy version of escorting than a realistic representation of the job.
Someone might initially attract a handful of clients who fit that description but the pool of gay, wealthy, attractive men who regularly hire escorts is inevitably quite small. And even wealthy clients who hire escorts typically value variety and zero strings attached rather than committing to one provider indefinitely. Having money and options means they can easily move on to someone new.
The gay escort market is also heavily segmented by looks, age, body type, and specific archetypes. The "fresh 18" appeal probably has one of the steepest depreciation curves of all.
Put it all together: a small target market, high client turnover, a rapidly diminishing youth advantage and constant competition from newer faces. That's a business model with a ceiling and an expiration date, not a particularly reliable long-term career.