I have to admit that I am interested in your progress. Contingent upon regaining at least a Class III Med. Cert. I will be looking around for an airplane myself, so I thought that I might throw out a couple of my own ideas to see what you think about it, and to see how others on this board may have handled it.
First of all for my pilot qualifications: ASMEL/RWMEL, Instrument Rating in both fixed and rotary-wing aircraft and Type Certificates for a Boeing 234 & Sikorski S-76. Total Flight Time ~9,000 hrs., ~65% RW & 35% FW. Virtually all of the RW time is turbine-powered, multi-engine helicopter while the FW time is ~60% SEL & 30% MEL. Total Instrument Time is ~1500 hrs.
What I am looking for is a multi-engine aircraft, with a range >1,200 nm that has the capacity to hold 4-6 adults. Since anything in this class will be "outrageously" expensive to own as an individual, I am looking for proportional ownership of an aircraft as described, with a group of 4-6 people with somewhat similar flying experience (to keep the insurance rates from costing more than the airplane itself). I can wrangle up 1 or 2 other pilots that I flew with while in the military, so it will be an adventure finding the other 2-4 partners that we can all get along with each other, and would be just as happy if I could find a military flying club that had at least one airplane that met my needs.
Bentley & I will be watching your progress, perhaps adding a comment or two, and/or even asking a question as I/we move ahead, perhaps at a bit slower pace than you are intending to do so, but hopefully successfully "piggybacking" off of your experiences and opportunities.
I would agree with the comment that you will probably need to spend more than the $40,000 that you are budgeting to acquire a plane that will meet your requirements as specified, and even if you found one that appeared to be able to do everything that you wanted its condition would be such that you would be spending more in repairs, maintenance, and upgrades than would be necessary for you have a reliable, safe and comfortable aircraft to fly. Perhaps you might do well to consider something along the lines of proportional ownership unless you will be using it as a corporate aircraft for your business, or have a lot of free time on your hands and really need an availability rate for your own use that would make such a "shared-usage" impractical. My thoughts are that I would rather fly the airplane that I really liked and that met my needs even though I could not afford to own it on my own than to buy a lesser aircraft and always be unhappy with the one that I could unilaterally afford to own. How many hours do you intend to fly the airplane that you will be purchasing? I am pretty much semi-retired now, and can virtually make my own schedule, but I doubt if my utilization rate for an airplane per annum would be sufficient to justify owning one on my own. Of course, should I hit one of those multi-hundred million dollar Powerball drawings one day my Jetstar 731 Series II will share my own private hangar with my S-76, and some version of a ruggedized piston or turbo-prop iteration like a Twin Otter, and I will be able to own 100% of each of them, but until then cooler heads, and more realistic bank account balances, must prevail.