Twinkies are a good choice....if you get the right Twinkie. Nothing wrong at all with a 50+ YO airframe...if you get one that's had the TLC. Get the wrong one, and it will eat your lunch.
Twins are a bargain these days. Gas got cheap, so if you want, you can roll the dice to see if it stays that way. If you are a professional pilot of any sort, the single vs twin debate is moot.
A normal SE breed is a 90% dispatch airframe. As a pro pilot, you will tend to manage your risks to a greater extent. You know that a trip over a wide area of low IFR probably isn't a good idea, along with night low IFR or over any kind of terrain. You, individually might take that risk, but it will get some second thoughts if you're taking your family with you. There's always the Cirrus option...but don't forget to add the 10 year repack into the cost of MX. You're not going to tangle with TRWs, which in Florida 8 months out of a year are legion. Trying to dodge them with XM or FIS data is a VERY bad idea. Ice of any kind is going to park you.
A piston twin, on the other hand, will probably move that number up to 95% IF you get one with de-ice and radar. You'll feel far more comfortable with the maybe/maybe not marginal situations.
As an aside, TKS is a nice...but unless the airplane already has it, it is prohibitively expensive to install.
I've got a turbo Bonanza. Back up alternator, Sat weather, Stormscope. NICE autopilot, WAAS GPS, ADSB in/out. With all that capability, I still won't take it LOW IFR unless I know I've got an out that's easily reachable. Low IFR the whole way is out of the question. TRWs need a clear path to deviate around. Ice is a non-starter.
I don't add up the cost, but it's probably the same as ATNs Mooney for the ancillary stuff...at the present. I spent some coin over the years to bring it to spec. Plan at least 15% of the purchase price to do the same. Non upgrade cost at annual time is about 3k. Hangars are spendy here so that's another 3.5k. Databases and sat WX subscription is another 1k. Fuel is $4.50 x 17 GPH for 190 knots true.
Good mechanical condition of the airframe trumps all, and it is wildly divergent. Buy the airplane that is set up the way you want already. Adding avionics and other items later is an immediate 50% upside down proposition...a waste. Paint and interior are the easiest and least expensive things to address. Get an A&P who is VERY familiar with the type to do a pre-purchase. Most airplanes have dealbreakers that will nail you financially if missed.
If you didn't want to roll the dice on a Twinkie, but wanted a twin, you could probably find a decent Seminole or Duchii. Beware each has airframe life limits. Senecas are nice, but a nice B-55 is probably in the same price range, and O-470s are solid. Finding radar in a Baron or Seneca is far more likely. Boots on short bodied Baron are kind of rarish unless it's a C/D/E.
Richman