My wife is not in favor of having contractors work on the rental during vacancies, doing showings during the Pandemic, so this suit us fine.

While there is no black-and-white safe harbor rule for your circumstances, I have a feeling that we could interpret these Regulations in your favor. 

Some owners pool a lot of assets under a large policy, so their premium may be much lower than yours, or vice versa.Additionally, with the supply/demand dynamics favoring sellers currently, you will see properties selling for what they can generate, not what they are generating.  

Once you have it furnished or decorated to your style, do yourself a HUGE favor and get professional photos taken.

But that longer time horizon can actually work in your favor.1.

If that's the case, you can get an experienced partner by agreeing to a profit split heavily in favor of the veteran investor.In exchange for a smaller profit, you get to shadow the investor throughout the entire process.

The numbers pencil out in favor of short-term renting but I’m curious to know how long it typically takes to ramp up a short-term rental.

It sounds like you got a pretty solid case in your favor.

Most banks will not look favorably on a business that is "younger" than 2 years old.

While Dubai may have some of these key points (pre-COVID) I would question the reliability of the data produced and argue that there are more preferable places with a long-standing and respected legal system that does not favor certain individuals.