Any 500 series Citation can be flown single pilot. DO NOT get a 551. Waste of money.
The way it works: The 501SP and 551SP are single pilot certified airplanes. Check the flight manual, and under the 'required crewmembers' you'll see that only 1 is needed. Basically, if you have a CE-500 type rating, all you do is hop in the seat all by yourself and you are good to go. No special training required. All other 500's you'll see that under the same section 2 crewmembers are needed. However, you can get around this with a single pilot waiver, which Simuflite or Flightsafety can help you with. Any 500 series Citation, from a straight CE-500 all the way up to a CE-560 Encore+ can be operated single pilot with a waiver. It's not hard to get either.
The reason I say DON'T GET A CE-551 is because in order for the airplane to get type certificated as a single pilot aircraft, the MGTOW had to be certified no more than 12,500 lbs. That is the MTOW for a CE-551. I've never seen the books on one, but if it's anything like the CE-550, you DEFINITELY don't want it. The straight older CE-550 aircraft have a MTOW of 13,300 lbs. If you fill it full of gas, you have about a 200 lb payload.....and that's not getting into CG issues. Now knock about 800 lbs off of that and you are left with being able to carry about 4,000 lbs of fuel in a CE-551 with 1 pax and a pilot. That SUCKS. Depending on how much money you want to spend, you can get an older CE-550 with a weight mod on it (up to 14,500 lbs) get a single pilot waiver, and put whatever you want in it. The SII is still just a CE-550, same type rating, same single pilot rules. Difference is the takeoff weight is higher, the engines are a bit bigger, and it's a .65 or .67 airplane vs. a .62 or .63 airplane in the regular 550's. However, the TKS wing anti-ice system is a piece of crap, and you'll be hard pressed to find one without corrosion.
If you want to get into the CJ series, there are 2 seperate type ratings you can get. The CE-525 type covers you in all the CJ's, and the CE-525S type rating covers you in all the CJ's single pilot. No waiver required with that type rating.
All depends on how much $$$$$ your boss wants to spend. The BE-200 will definitely cost you a ton less money to operate, but the Citation will give you an extra 100 knots. Don't just look at cost per hour, look at cost per mile. Say the Kingair costs you $1000 bucks an hour and the Citation costs you $1400 bucks an hour. The hour in the Kingair will get you about 200 NM, whereas the hour in the Citation will get you about 300 NM. Do the math and that's a $5.00 a mile cost for the Kingair vs. a $4.66 a mile cost for the Citation. Pretty big difference. Of course, that is just a very rough estimate. All I'm saying is don't get hung up on one thing and let that make the decision for you.
Good luck!