@Liam DelumpaI have out-of-state properties, but all are single-family homes that my family and I lived in for a few years and then turned into a rental when the military sent us to a new duty station. 

Your agent should advise on at least these topics probably more, this would be someone having fiduciary duty to you. 

Social media and virtual networking is vital for at least getting the conversation started.

There are different things to take in to consideration in every market, but I believe that most of the markets mentioned so far are relatively similar.Retaining tenants is vital to consistent cash flow.

It is vital to work with an experienced team of attorney/title company that know how to conduct a double closing and follow your closing instructions to AVOID release of your funds in Transaction A before the monies from the end buyer of Transaction B is sitting in escrow at the Title company.  

Since this will be a vacation rental, it's vital I have a good cleaning service who responds rapidly and timely.Thank you for any recommendations!

Very vital step in them recovering respectability and being able to function effectively in the future.

I feel wholesaling is a vital part of learning to invest in real estate for long term wealth attainment.

If you are too highly leveraged, then your debt service may create a negative cash flow, but it is vitally important to understand that the issue isnt with the property, it is with the individual person taking on a highly leveraged position.There are ways to improve the amount of rent a property can yield in certain circumstances as well. 

Of course, my example assumes there is a property management company in place that is handling all administrative and management duties of the business.