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Drew, many of the people here have lots of time, but a couple, don hickman and myself, went straight in.
First, you must get your private pilot rating in a 172/152/etc, type aircraft. That's a because. The SEL (Single Engine Land) rating is the basic building block.
Once you get your license, you should, honestly, go out an fly some in the 172, because, as someone is fond of saying, the license is a license to learn. I would suggest another 20-30 hours of renting, as a minimum.
From there, you can do MEL. That's Multi Engine Land. There are several ways to do this. Don and I chose different paths. Don got an instructor, and flew his aircraft with an instructor, then did the checkride, ending up with Multi Engine, Center Line Thrust rating. I went to one of the ME schools, mills, I went to the one in Texas, and at the end of the week, I had my Multi Engine rating. Notice no restriction on Center Line Thrust. Not a big deal to me, unless someday I buy a twin engine jet (NOT LIKELY). The big difference is that it is difficult to find an FAA examiner who can do the ME checkride in the skymaster. Also, during the check ride, you are supposed to feather an engine, and re start it. Practicing all that places a lot of strain on the engine. I chose to do it in someone else's airplane. Also, the mills are flat fee, quick, accelerated study, don't worry about the plane in for oil change, etc, because they do the maintenance.
Once you are MEL rated, you can take the skymaster anywhere.
You asked, good cross country machine??
Well, one of the folks who is presenting at Nashville has flown to Europe. That's sort of cross COUNTRIES.
We did a fly-in in the bahamas last year, and my wife and I flew from Michigan to the Bahamas.
Chachi flew his from Panama to the Bahamas. Don regularly flies from Indiana to Cancun, Mexico.
There is a side bar, with a section called Articles. You can read some there.
Owning a plane, like the skymaster, gives you a 'freedom' to do things that you would not normally consider. My wife needed hip replacement surgery, and the local docs said, wait as long as you can, because it needs to be redone in 10-15 years. I found a doc in NYC, at Columbia, who was heading the clinical trials on a new process. I spoke to him on a Friday, he said I can see you next Thursday. We went to NYC the next thursday. It was Thursday, September 12, 2002.
Anyway, I have written a lot. There are others who will write more.