Quote from @Jacklyn Robins: Sorry, I clearly misunderstood your level of experience.

Ask how many units they manage and how much experience they have.

Talking DOM is a 'blah, blah, blah' experience with landlords. 

With 30 years of experience in real estate and now owning a quadplex, duplex, and a condo STR, you’ve already built an impressive portfolio.

Does anyone have any experience of getting into real estate this way?

I have no experience there. 

They claim to market on dozens of online channels, and they seem to know the right amenities to feature, have great design, services, experiences etc.

Quote from @Drew Mullin: I have some experience in the south Florida area.

In order to get there it would be good if you could keep feeding cashflow proceeds back into acquisitions, on top of your continued W2.Speaking from experience, you can manage probably 30-50 units yourself nights and weekends before you really need to hire someone.

To do that you can't just quadruple your prices, you have to quadruple the experience.