Marpoo Sorry if my response sounded negative, probably cynical after seeing similar things before and being approached by pilots with their Dads asking "If I bought a twin for my son would you opearte it and let him do most of the flying in it".
Also personal knowledge of Dads buying twins to kickstart son's career.
Didn't realise you were considering self funding, but the cheaper twins have proved to be financially unviable in charter.
If you study the resale/for sale price of GA twins you will find that the most financially successful and practical charter aircraft are also the most expensive, market forces at work.
So a good twin is going to hit you around $250,000 or more, and is going to cost you around $400/hr to operate before profit, loan repayments, $50 landing fees at most aboriginal community airstrips, and you probably want to earn something for yourself as well, so you need to budget on achieving a minimum of 700 hrs/year.
In two years you're most likely up for two engine overhauls @ $50,000 each, and two prop overhauls @ $8,000 each. (this is included in the $400/ hr cost above, but you probably won't have zero time engines or props on what your budget says you can buy.
You will need to budget $20,000 every 6 years for repaint and reupholster, and expect your 1st 100 hrly to cost around $12,000 if you take it to a maintenance shop that hasn't already been working on it before.
You're better off flying someone else's and spending your money sensibly on wine women and song instead of frittering it away on frivolous things such as aeroplanes, even a divorce is cheaper than owning and operating a twin.
Seriously though, if you win lotto, give it a go, it'll keep you in your comfort zone instead of you spending all that money on something that might give a reasonable return on investment.
So please, at the risk of again being thought negative, I'm really being positive and trying to stop you becoming an undischarged bankruptee.