Overall, if you aren't meeting the 1% rule, I wouldn't do it, but, of course, there are exceptions to the rule.It’s hard to find 1% deals anywhere in current market conditions.

They are hyper focused on any conforming loans $500k-$10M and apparently most of the coast is currently a 'preferred' high limit area for some of their investors.

There is a bill currently in legislation in Hawaii County that is changing several items that affect rentals.

(Currently looking at Samana province).

Currently we have a 78 year old property manager who makes 10% of the rent for doing everying....He is adverse to technology so sharing the work load with him through turbo tenant usage is not possible.  

I have an area in mind that is currently undesirable but based on market trends seems to be primed for growth in the next 5 years.Any advice on research I could conduct before diving in, or other avenues I could explore to start and build my portfolio would be greatly appreciated.

Some lenders will waive escrow accounts- some for free depending on the loan product and down payment and some with a .25 add to the current rate. 

We are currently looking into Kissimmee and Fort Myers to start with.

However, this book talks about getting a margin of $20,000 to $30,000 off a property off rip and from what my understanding is, the current housing market wont allow for that I will lose that deal most times.

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.