Your story sounds alot like me. While not a Gen 5, the Gen 2 B/W GTS was my dream. I grew up super poor(like trailer house poor). I am not one of the SVTP ballers, There are tons on here that do way better than I do, but I am happy with how I have done. The Viper was the car that "got my into cars". I bought mine after my dad died. My dad worked, and just saved. My dad died in a accident in 2013. Before he died he always talked about getting a 1967 Camaro RS/SS. this was his goal/dream to have. He never did anything else, he worked, and worked, and after he died my step mother got all the money from the house, and insurance, ex-communicated my brother, my sister, and I, moved and had a big ass house built in AZ. After that I kinda realized that I could go at any day. And I believe that changed me. Soon after that I started looking for mine. Luckily I have a awesome wife who supports me. Some of the comments on here about get one now before you have kids I don't agree with. I got mine when my daughter was 4. My wife was 100% behind it, and I was making way less than I do now.
Here are some things:
Never meet your hero's: Again I have a Gen 2 not a Gen 5, but I actually thought the same thing before as I never drove a Viper before buying one. I bought mine in 2014, and every time I drive it it makes me happy. EVERY SINGLE TIME. I always get people who say things like " Oh I drove my dad's friends Viper, and they handle like crap". I have had mine on AutoX, and open track. These people are full of it. Are there better handling cars? I am sure there are. It also depends on your definition on what good handling is. On track mine kinda likes to be steered with the rear in a way at times. Not a bad way, but you can use it to rotate the car mid corner sometimes. I won't get to into it cause it's a gen 2 vs a Gen 5. What I am trying to say is the "Never meet your hero's" has never applied to me in my ownership.
I also own a 2016 GT350. Now I will say it is a GREAT car, but the Viper just has something that the 350 will never have. One of those things I can't really quantify. It's just way more special.
The "You Made It" goal is exactly how I felt when I got mine. The first week + after I got it I just kept going out into the garage, and looking/sitting in it for hours (and I do mean hours) My wife laughed at me quite a bit. I now have a 2016 GT350, 2012 Mustang GT Track Car, a couple race gokarts, and have had a few sportbikes. If everything went to shit, and I had to for some reason, or another liquidate stuff. The Viper would stay. It would be the only one.
In the end it is your decision/money. I feel fortunate that I got to make my dream happen. A lot of people will never get that chance, and we are only alive once. Good luck man.
Definitely similar stories. I'm sure you have some interesting childhood memories to go along with it. For instance, I remember how quickly I could close the blinds and hide if I saw a tax man pulling in the driveway. That kind of stuff has an effect and I often wonder if it is why I have such a tendency to hoard money. Sorry to hear about your dad...
I'll add that I'm pretty open on anything from a Gen 2 GTS all the way up to a Gen 5. I've had probably a dozen hours or so of seat time in a Gen 2 and maybe 30 minutes in a Gen 3 Coupe and that is about it. I loved every second I was in either car and, like you said, I just haven't been able to replicate that feeling in any other car I've been able to drive. In fact, a Gen 2/3/4 might be a more realistic option since the thought of being responsible for a 100K car is enough to make me light headed. If I had an out of warranty bearing failure on a Gen 5, I'd be cooked.
Thanks for the story and the feedback. The whole post kind of hit home for me.