Having bought planes for the boss...unless there are other factors, like 'we need to spend this amount of money' or 'we can only spend this'...you do need to specify a budget, or you will be chasing planes all over.
Single pilot., 3-6 pax, going in and out of 3000 ft fields...is at the ragged edge of most jets minimum runway requirements, and beyond 99.9999% of most single pilot jet captains...I know, I had six SP waivers from 550s to Ultras.....if you typical turboprop captain tries to land at 100 kts..he's gonna have a hard time stopping that King Air in 2500 ft...so much of this discussion really centers on the pilot you have...if he's a hot shot...then you can buy more plane...
You mention you need glass cockpit..but not pressurization...that's a bush league move and tells me that your more worried about gear to tell you where you are then being comfortable in the cabin..
All this said...for me, with this type of profile, money no object...I would probably get a Conquest 1...you don't get the Conquest two as your not going to have that APU at a 2500ft field...and Garrets need love...PT6s are bullet proof...if your pilot is weak ...a 421 will live in the shop due to shock cooling and such...so a C340/414 is better...as we go down the line, if turbochargers are too much for this guy..then something like an Aztec would be pretty bullet proof for him to learn on...it twins are beyond him...a Lance...could carry the peeps, make the range, and get into those runways....
If your pilot needs a Glass cockpit, but is willing to forgo twins, pressurization, ect....I would suggest renting van at the airport...and just driving to your destination...