Great advice and will check out the software

Having tried several software programs including Landlord Cash Flow analyzer and Michael Blanks Deal Analyzer, I am looking for something that is more in depth with the value add component. 

Supposing I would use several sites to advertise my short term rental, would someone recommend software to keep all of the bookings on one calendar that does so in real time? 

A lot of landlords turn their heads towards that requirement and use their personal accounts.Landlord Software:  There are several software companies available that offer rent collection, plus additional features. 

Any landlord software company will be able to provide them.However you're talking commercial.  

Can anyone recommend a property management software/app that allows the tenant to pay rent and it is immediately deducted from their account?

SO is a software engineer.

Great question; I don't have any PM recommendations directly in Sarasota, but since it sounds like you're going to be buying a rental property and won't be able to move in for about 6 months or so, it might be a good idea to consider a landlord software that allows you to automate a large part of this process.

What type of software or application can be used to accomplish this task?

Once you do decide to procure your first rental, definitely lean on the BiggerPockets community as a resource; I'll also say that it could be worth considering a shot at a software solution built for DIY landlords (1 - 15 units) to bring some automation to the rental management process (just to make things much much easier for you)!