What should I replace my 1995 Viper with?

Look into the R129 Mercedes 600SL convertible. They look cool and those quad-cam V12 engines are awesome.

Shelby cobra replica? Side pipes! 

BTW, big fan of your post!

"Looking for a fast, MUST be convertible, not a project"

Also you "first maybe a pickup truck that I put a drivetrain in".

Cobra?  Already built.  Although a Viper is essentially a slightly watered down Cobra, it could be fun to experience the original intent for a few years.  A well-executed and sorted kit seems to hold it's value well.

308 GT targa top. Don't think they made them as a true convertible. 

Or this with a ton of boost. Different?  Yes. Cool. .. well ok that is subjective. Rare?  Yes as they have all rusted away. I guarantee you would be the only one at the cars and coffee. 
 

Aston.  

93EXCivic said:

Oddball JDM: 2nd gen Toyota Soarer Aerocabin 

Yooo these are so cool. Did these ever get the JZ engine? 

The Viper wasn't the only Mopar Image Car of that era.  If wanting to say in that vein, the Plymouth Prowler might not be a bad choice given your criteria.  It too is certainly a rolling carnival act drawing attention everywhere it goes.  Someone here once said that the used market on them is a "never loose money" type of ownership.  I especially like them with the front bumper delete like this:

The Chrysler car of that era wa the Crossfire but less "spectacular"

GM got in on the game too with the SSR which might meet your criteria too: 

With the mention of Chevy C10 truck you might consider a K5 Blazer but a great one will likely require all the budget.  However, I don't see them losing value anytime soon.  

In reply to John Welsh (Moderate Supporter) :

You forgot one :P

A couple people beat me to it, but I'd look hard at a FFR Cobra for your requirements.

Staying along the lines of old GM's, the last of the big girls are awesome too.  They certainly address that issue of no trunk space...

Eldorado too: 

BlueInGreen - Jon (Forum Supporter) said:

In reply to John Welsh (Moderate Supporter) :

You forgot one :P

And forgot another (intentionally)... 

Good luck finding parts for a 3000GT VR4 Spyder. When I worked for Mitsubishi in 2002, they had a car there just for parts. I couldn't fit reach the steering wheel and not have my head hit the roof and I'm 5'9".  Ergonomics are not good. 

Have any of these made it state side?  https://www.donkervoort.com/en/

rodknock said:

93EXCivic said:

Oddball JDM: 2nd gen Toyota Soarer Aerocabin 

Yooo these are so cool. Did these ever get the JZ engine? 

 

No that gen of Soarer didn't get any JZ engines. It had the 7M-GTE engine. They only built like 500 of them though.

Lotus 2-eleven too racy? 

This ? :

If you want super impractical V8 Exocet. It defiantly turns heads and is brutally fast.

3000GT's are garbage.  Run away.  You're not going to get an NSX or a Mk4 Supra for your budget unfortunately.  E46 M3 convertibles are nice, as are 911 Carrera Targas.  With the 911 you won't lose money on it either...

GTR swap a Murano Cross Cabriolet

Left field option:  A nicely sorted TR6?  While any vintage LBC will be a project to some extent, your budget would afford a very nice one that shouldn't need much fiddling. 

I like the R8 vert as well.  Put exhaust on it and enjoy

Placemotorsports said:

I like the R8 vert as well.  Put exhaust on it and enjoy

I would too if it existed for $50k. Cheapest 'vert in the country via autotrader = $70k. 

Placemotorsports said:

I like the R8 vert as well.  Put exhaust on it and enjoy

Are R8 verts sub $50k these days, per OP budget? Around here, $75-77K is the lowest I see the ragged out ones.

Olemiss540 said:

Placemotorsports said:

I like the R8 vert as well.  Put exhaust on it and enjoy

I would too if it existed for $50k. Cheapest 'vert in the country via autotrader = $70k. 

And you don't want the cheapest one. It's cheap for a reason.