Quote from @Joy Daniels: I manage short-term rentals in the Sarasota area, and I'm always looking for innovative ways to boost occupancy rates year-round.From your experience, what marketing strategies have had the biggest impact on keeping your properties booked?

Our portfolio currently cash flows, but cash flow isn’t our top priority right now since we plan to use this portfolio to supplement our retirement in 12 years when I leave the Army.My biggest challenge is committing to an out-of-state market.

There are so many variables and some of the biggest misunderstandings come from regional variances on how these variables are handled (mortgages & financing especially).I had thought progressing towards multifamily and then commercial was the obvious path to follow, but one conversation changed it all.

That will likely make the biggest difference on if it cash flows or not.

We placed our biggest bet on a single property, class B shares.

My biggest piece of advice would be to find someone who is in the position you would want to be in 10, 15, or 20 years and meet for coffee.

It was my biggest problem as a GC.

@Mindy PerryReally doesn't matter what software you pick as long as it has the features you want.Two biggest challenges with ALL software:1) None are perfect, so deal with the tradeoffs2) Most users rarely put in enough time to really understand how to utilize the software.

The biggest mistake people make is not having enough reserves before going into real estate investments.

My biggest question when I was researching all the programs was "If these people are so successful at what they do, why are they charging so much for all of this and always trying to upsell?"