If every renter on the street had significant free money to invest, why wouldn't the landlords increase rent? The only thing stopping them is the availability of other land / houses to buy, which acts as leverage for the renters. As land gets bought up over time, zoning becomes more restrictive, etc and this source of leverage dries up.
The result is that while some high-income earners benefit from renting, it is mathematically impossible for the average person to do so. 'Anyone can win the race but not everyone' principle.