I have never flown a 530 or 505 or even the 350.
I did fly the 500D/E models and the 206B long enough to compare those two.
Thus far there has been a pretty good discussion of the various merits and demerits of several different choices.
I would imagine the 530 would still be the same re pilot happiness but would require some maintenance in excess to that of the Bell Models.
Bell models have more room in the back seat and of course baggage room....and unless there has been a real change in the TT Straps time life that can add a lot of expense for a low annual time operator.
Being a penny pincher I find myself leaning towards a Bell L-4 or better a good used 407.
The final analysis is up to the buyer.....doing his research on purchase price, cost per flight hour (operating costs) and Fixed Costs, available of local maintenance and distance from a Factory Authorized Service Center.
The 530 is a hot rod no doubt but it is not much for going somewhere with family and baggage....ski's as it is short legged. That can be improved by adding a baggage pod and Internal Fuel Tank but that adds weight and of course cost.
The mention of Auto Pilots etc as found in the 505 is an important issue if you are a new helicopter pilot and you are going to have your family join you.
A 407 with the same level of avionics (or nearly) and maintaining proficiency in using all of the features to the maximum extent possible would also work towards being the insurance policy "rotor rookie" is describing.
I did a wander through a Trade Paper advertising Helicopters that are for sale currently led me to focus upon the 407 due to the various. prices of all of the suggested models of helicopters being discussed.
For you hot rod drivers....think about an MBB-BO-105LS....only about 58 of them built if my source is correct but that gives you two engines rigid rotor, German engineering, and LOTS of power.