I'm thinking on getting the following bugeye and a 2+2 3000 and a 2002 viper GTS ACR.
That's quite an instant collection if you are thinking of all 3. Otherwise, it is quite the diverse set of choices. An adult cannot sit in the rear of a Healey with the top up so it's for small children only. As far as I am concerned, that is a parcel shelf and none of the 3 are practical choices if you are thinking of taking your chick friends out for a picnic.
This may be controversial, but IMO, people are happiest when their choice of a collector car matches the image they wish to project of themselves. I know people with all 3 of those cars and they provide a completely different experience, both in terms of driving and image.
Bugeyes are a bit dangerous as a road car and they are uncomfortable for long trips. They are great for a mountain dash and they do make good vintage racers but you will be the lowest rung on the ladder. A 1275 Bugeye (heresy, I know), will be competitive in some groups but a 948 will be the slowest car in almost any group. They are fun, cute, and inexpensive. If you are cool with that image, why would you ever consider a Viper?
A 3000 is a great GT car but not very sporting. Once again, just my opinion as an owner of a Healey and other cars. If you want to drive places (tours, mountain drives, etc.) it's a great car. People will not assume you are a rich snob as they would with a Jag or Aston (or Viper). If you want a real sports car (think autocross or canyon carving), try a Lotus Elan. I wouldn't even think about racing a big Healey, but it can be done with some success.
The Viper is a very fun and fast car but you will be lumped into the gold chain crowd. It is a real performance automobile but it may be perceived as a look-at-me image grab. Give it 10 more years and it will be the next Pantera.