I agree with GG, you will need a CP to set you up and manage it for you, listen to him/her.
That's not want you want, do here goes...
If it was me I would use an R44 clipper to cover two pax scenics and shuttles and an AS350 for larger loads and other airwork. It gives the junior pilot something to progress to and a nice machine for you to fly as well. Let's face it, you are probably going to do a lot the flying eventually.
Go for a ride in an AS350 and see what you think. Talk to an engineer about maintenance/running costs of each.
Matching aircraft is nice, but if you want to grow plan for it!
Good luck, I hope it works out.