I think as a private aircraft from new or with known history the R22 won't set a foot wrong. Or better still syndicate into an R44 consortium. Both are quick, capable and reliable. Give the R44 a chance and most people realise its an incredible machine, and pretty much unbeatable on cost per seat per mile.
You can count the number of times I've been in Enstroms on one hand making this a grossly unfair generalisation but they just always appear to be a permanent fixture in the maintenance hangar.
And if you have a 300 C that thrashed engine will not go to 1500 hours, let alone the extension. Furthermore any H269 kept outside in the UK you can double your maintenance costs. And you just aren't going anywhere quickly in one despite feeling like you are pointing straight down at the earth hanging off your harness. This increases your trip cost even if cost per hour is less. Luggage? Isn't happening, unless you like flying from the left and precariously mounting it up between the seats. It was a trainer. An excellent trainer. But not a practical personal transport.
I reserve judgement on the Hiller. On paper it doesn't look at all practical. But neither is its cousin the Bell 47 ... but I would have one in a heartbeat if I could.
Rotorway anyone?
All IMHO