Hey Beachgal5...welcome to the board!
You'll be just fine...there's nothing unusual about asking someone to accommodate you around town or on activities etc...it's quite common.
Your best bet would be to hire one of the tour drivers/guides from Negril.com,
http://negril.com/transport/, as they've been vetted by the staff, the many boardies of Negril.com and Rob and I (Lisa) know them all personally. Though, I wouldn't really worry about hiring any legal red plated taxi, unless you're stepping out of the regular beach or West End locations or moving around quite a bit at night.
The hotel and bar staff at properties in Negril are quite protective of their guests...if hustlers are bothering you, a "no thanks" will generally stop them...but if they continue, please don't hesitate to let a staff member know you are being bothered...they will put a quick stop to it for you.
As far as carrying your money...I carry a purse here all the time, but many women do carry their money in their bra (called a granny purse here
) or you can easily carry a crossbody purse (get one with thick straps) or the infamous and now popular again, fanny pack. You can use your phone with no problem as most are aware phones are locked up and traceable...but just like anything don't leave your phone lying around for
anyone to take.
Based on the information you've provided...I think you're going to have an absolutely fabulous time...you seem aware, inquisitive and ready to explore!! EnJoY!