If you’re leading it to a company be sure to have in your lease explicit information about who is responsible for what in terms of maintenance.

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

It was purchased from MLS as a long term buy and hold rental.

As long as the wholesaler is direct with the seller and the deal is real, go for it.

Since I am entering this field in the latter part of my life (63), I do not want 'long-term' investments as I am not interested in making millions, but having enough for the remainder of my life to 'Vive La Vida Loca'!

But, it is bad for landlords, long-term.

As far as the bedbug cost, I would consider how long you are willing to let the place sit empty. 

@Rebecca GonaBigger Pockets is a great place to find a tax accountant that specializes in short-term rentals. 

Rates:$2,000 Daily$10,000 Weekly$30,000 Monthly$25,000 Long Term Monthly$3,000 Holiday Daily$15,000 Holiday WeeklyI am looking for insight for anyone who has experience in this market to see how realistic that is... 

I would also weigh if you plan on staying in the home you are in now for a long time or move in the next 5 years.