The primary difference between these groups of people is their level of optimism.  

If you want more cashflow, I would optimize for the highest rent to price.

What if you pay off the loan in 2-3 years, because taking a 60 month loan on a depreciating asset is a sub optimal choice?

However, I started taking it seriously as a business on the first day and I've been optimizing it since then.

You are definitely in an optimal position - I am sure there are other bachelors who just need a room space, with couple other guys keeping the peace.

We have found the biggest benefits of self-managing our rental properties to be:1) Exponentially Higher Cash Flow2) Higher Quality tenants and therefore rentals3) More time freedom from your optimally performing portfolioAre you self-managing or using a property manager for your rental properties?

Not everyone optimizes for return :) We see it all of the time.

In my view it takes nearly a year to obtain the reviews that achieve near optimal bookings. 

The growth of the cash value in a permanent life insurance optimized for LIRP is only in the 3 to 8% IRR depending on the product.

You just need to make sure that you have enough cash flow to put the same premium every year for at least 5 years to optimize the cost.