In my general experience bigger is always better in STR's - do it when and if possible. 

I am no professional here, just explaining from my experience.. first, insurance starts claim and they send adjuster out to assess, check damages, and collect documentation.

@Charles EvansFrom my experience, having rental income of $1,400 to offset a $2,600 mortgage, leaving you with a $1,200 payment, is a manageable setup with an income-to-mortgage ratio of 28.5%.

Her recommendation made me loose confidence in her experience.

Fannie Mae only requires ONE year of property ownership or management experience to allow you to use rent to qualify.

You've got the experience and track record.

I can only speak to the Texas market, where malls that focus on creating consumer experiences (coffee shops, kids play area, entertainment-based tenants) are still performing well even in this age of online shopping.  

Try to get some experience by helping your friend with some of his projects.

In our experience, things move in ebbs and flows and the speed of rental depends on your asking rents relative to competition.For example, there was a period of several months at one of our properties when a 3 or 4 BR unit came on the market it rented almost instantly. 

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.