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Great Question!
While no expert in Skymasters compared to the many long-timers on this site, I may be able to offer some perspective because I went through a similar thought process that you are struggling with now, about 2.5 years ago when I bought my Skymaster. I didn't have an engine out in a single like you thankfully got through OK, but once I got to flying IFR with my family, I never got comfortable in the soup on one engine. My wife was similar and the kids just had blind trust in dad given their ages, but overall the whole crew never got terribly comfortable. I was flying a DA-40 in a partnership and it was time to move on from that right about the same time I was reaching the conclusion I would not be comfortable IFR on one engine. I gave a lot of thought to the chute concept as an alternative but honestly I did not look that seriously at the CIRRUS as an option. I know there has been lots written about CIRRUS and all the accidents, lots of debate about bad pilots versus bad airplane and all that. Who knows the real answer but where I landed on this was to conclude that CIRRUS was just a little too new for my liking. Their craft have developed with wing changes over the model years, a very high number of SB's and the ongoing debates about the flying characteristics generally (including the spin testing, which some say was a primary reason for the chute and their ultimate certification with it). My own theory on the CIRRUS is that it is basically a crappy "seat of the pants" airplane. I could never get a good control feel from the side yoke and the lack of manual trim didn't help. It seems almost like the intent was to have the autopilot fly the plane while you play with all the fancy electronics. Of course the autopilot didn't need a trim wheel, but a real pilot might like one! So convinced I would never truly be comfortable in a CIRRUS (particularly perhaps an early cheaper used one), so I moved on to Cessna.
The 182 with a BRS chute added was in my view a viable alternative to the CIRRUS (and vs a Skymaster, perhaps). In fact I was intending to go the route of the 182 with a chute when I got intrigued by a Skymaster for sale that was very well equipped. I won't walk you through all the various thoughts on 182's but I looked at many before the Skymaster idea took hold. In the end the 182 is a great and very versatile airplane, but the BRS installation in it is an afterthought and it is a pretty clumsy install which eats up a considerable amount of the available baggage space.
So on to the Skymaster. I found an early example that basically had an incredible amount of money and effort put into it (thankfully by prior owners). I will leave it to those more informed to provide opinion on early versus late etc, but will say that from my perspective I don't quite understand why the early planes are considered less able. Mine doesn't have the high legal useful load because these increases came later, but it climbs like a banshee, can carry whatever I can reasonably stuff in it, and other than the door change is the same basic airplane, as far as I know? On the door, again no expert, but I understand while convenient they can leak and present other issues versus the simple side hinged unit.
In terms of cost, despite all the money having been spent on my plane prior to me (new interior, updated avionics, new paint, new engines and props), I haven't been that impressed with overall "reliability" and thus have been spending more money and down time than I like trying to de-bug small issues and get it stable. Part of it is that I am pretty picky and like things to be right but I have had my share of nuisance issues. In fairness many of the issues are systems related and not Skymaster related, per se, but as a package it has not been as reliable as I would like. Some examples:
- series of gear issues, anything from bad hoses, corroded hard lines, finicky rigging
- leak in vacuum line to MP gauge that took forever to sort out
- failure of switches (throttle position/gear warning/panel switches)
- problems with rear cowl flaps (switches and a bum cable)
- variety of avionics issues
Beyond that, I have replaced certain things that were not done prior and perhaps should have been given all the other upgrades done to the plane (eg all new gear hydraulic hoses, newly rebuilt powerpack).
Overall, I have spent about 2.5 times what I had previously been spending on the two prior singles that I have owned on (just) maintenance costs. Obviously fuel is about double and I am ignoring insurance in this discussion. My expectation and hope given the condition of the airplane I bought was that maintenance costs would be obviously more than a single, I had thought around 1.7 times the cost, not 2.5 times. I remain hopeful that once I get through the bugs it may stabilize to something like this level.
Overall, it will cost you more to maintain a Skymaster, but if you get a decent airplane I expect it won't put you in the poorhouse. Beyond that and back to your original question, IMHO, the Skymaster is significantly more airplane than a CIRRUS, particularly a $150K CIRRUS. There is no doubt that right now there are bargains out there for piston twins and the Skymaster is among them. You could get yourself a great airplane with great avionics, engines at both ends, and bank the difference in cost versus the CIRRUS as a maintenance and fuel reserve!
Good luck.
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