This is an important decision- I have a few PMs I can refer you to over here.- Depending on your budget, do you want a small condo or larger residence?  

I've done this so many times it is crazy, so speak with experience.Also in small towns trades can be tricky. 

We have trades we use on jobs and know what they will charge which is often considerably less than what Joe Homeowner would pay for the same job . . . the trades know we will be using them again and again. 

I'm an accountant by trade.

I would look at the value of the rentals before you make a decision to see if that makes sense for you.Regarding the furnishings, if you have to pay more for them (again here in FL, properties are generally listed fully furnished and you don't really get a discount to tell people to take the crap out - in fact, I had one guy refuse a good offer because one of my conditions was for them to take their crap!  

Here is a CSS Decision Diagram flowchart intended to bring together all the various questions when assessing the benefits of a Cost Segregation Study (via a professional or DIY).FYI - You can do a CSS for ~$400, ask @Malik Javed how.

The purchase decision might make itself clearer once you are here, have boots on the ground and are not pressured to make a decision from long distance.

Youre with WAY too many options and decisions at one gulp.

The weekly rentals were $8,000 (June) & $8,500 (July-August) As the summer season rental is approaching us, we are faced with a tough decision.

Making such a hasty decision on two weeks worth of knowing these people as your customers seems like a rash decision to me, but I don't know exactly what's going on, and sometimes personalities just do not mix well together.