Reorganizing the Fleet to get back into Motorsports - WWGRMD?

Trying to decide about if/how to reorganize my fleet of vehicles based on my very revised life situation and motorsport goals since moving from CA to OH and being busy in charge of production at a start-up brewery.

Goals:
Have a daily driver that is reasonably comfortable, practical, efficient, and fun.
Be able to haul some equipment (say 3 full-size kegs) to or from an event.
Be able to autocross and do track days.
(As much as I'd love to race wheel-to-wheel again, I don't think I have the time or energy to dedicate.)

Current Fleet:
Chevy Astro Van - winter beater and workhorse. I often haul kegs/equipment for work, but it's not my responsibility to use my personal vehicle for heavy lifting.
S2000 - Daily driver for spring through fall. Low mileage, near-creampuff. Solid for Auto-X, but is almost too nice to really thrash at a track.
Triumph Street Triple R - I hardly ride any more because all the roads here are strait and flat. It takes almost an hour to get to hills. I do not ride to work because I will probably drink something, and might need to carry something.

Option 1: Sell it all, and replace with 2 vehicles that split the difference.
I would get a 4-5 seater wagon - something like a MS3 or a WRX - to use as a DD year round. Not a full workhorse, but if I don't have a bike or a race car, I don't really need one. It would be enough to haul what is necessary for work, still be fun and relatively special, and a better GT car. Then, get a better toy for auto-x and the track. Something stripped out with proper rollover protection, but that is still street legal to drive to/from Mid Ohio. I'm seriously considering some sort of Lotus-7 style car for this, or a hot-rod Miata. I could even drive a 7 to work occasionally when I don't care about looking pretty, but would be nervous about riding a bike. This is an opportunity to check another vehicle off the bucket list.

Option 2a: Keep Fleet, get rollbar and track wheels/tires for S2000, wait to sell bike.
I'd be nervous that track prepping the nice S2000 will drop its value, and I'd still be bothered about getting it messed up at a track day.

Option 2b: Keep S2000 stock, sell bike, get track beater.
This takes up the most space. I am going to start house hunting soon, but I'd need one with parking for 4 cars. I'd get a less-cool track toy than Option 1. It would also be a track toy that would almost never be driven to work since I might as well just drive the S2000. I would also need to delay track days for longer, or just go do them in a bone-stock S2000 on summer street tires with stock rollover protection.

WWGRMD?

Option 1

My needs are similar to yours. I have my Focus for the fun stuff and just bought a Subaru Outback for the DD.

Option 1x: exocet

Keep the workhorse, "cage" the S2000, sell the bike to get a DD along the lines of a RSX or SE-R and go from there?

Option 1, but get a truck and a toy. Trust me, as a beer/wine/spirits salesman who does some deliveries, you don't want to be hauling multiple half barrels and jockey boxes in your somewhat nice DD.

My In-laws just traded their 2001 Tahoe and 2007 f150 in on a new f150 xl crew cab. Only options were a trailer hitch and he 5.0, but it's still a damn nice truck. With the back seats folded up a couple barrels will fit easily, and the rubber floors are easier to wash out.

Then buy a Miata and/or a shifter kart for autocross and track time.

If you want a Lotus 7 style car, check out the Westfields that Flyin Miata sells, they're a 1 donor kit based on Miata parts.

I would definitely sell the Speed Triple if you're not riding it.

A decent Lotus 7 car (unless you're talking Locost of potentially iffy parentage and build quality) is going to cost you $20k-$30k, which may crimp the overall budget somewhat.

I'd still say go for some kind of variation of Option 1 unless you know you'll have the space to go with option 2b. To me it doesn't sound like you're massively enthused by the thought of turning the S2000 into a track car, so I wouldn't do it.

A truck, a toy, a winter beater (optional)

Couple issues with "truck": The non-toy would need to be efficient enough for DD duty. I would kind of like to move out of the role of being the van guy at the brewery. I'm not getting paid any extra to haul all the equipment we need.

Not going to build a kit. I'm happy to wrench, but see it as a means to an end, not an end in itself. I like driving.

I'm aware of the cost on a good 7-style vehicle. We're in escrow now on a family parcel of land. I'll be getting a healthy chunk of change. I'm willing to budget a portion of it for a toy. The extra I'm looking at for my most expensive scenario is <10% of what I'll clear on the sale.

If you love the S2000, don't get rid of it.

If you aren't w2w racing, put a rollbar in the S2000 to track... or don't, you don't need a rollbar for track days.

The car is depreciating in value one way or another, are you really going to own a S2000 and NOT take it to the track? Something something being married to a pornstar something something.

I'll make it easy for you. How much for the S2000?

Ram Ecodiesel?

Don't get me wrong, I get you on the "I don't want to drive a truck everyday" thing, but when you toss in the "I need to haul multiple kegs" requirement it gets mighty nice to have a truck bed or van.

Side note, I once fit 7 1/6bbls in the back of my 2013 Mustang. You could probably put 1/2's in the other 3 seats, I often carried a 1/2bbl in the front passenger seat using the seatbelt to secure it, but the trunk won't close on a 1/2. BTDT, made a "no more 1/2bbls in my personal car" rule that only gets broken for my favorite accounts.

Replace Astro with 4 cylinder Ranger. I couldn't bare to part with the others because and replacement would be a pale comparison.

keep astro van; sell others and get S52 M coupe. Clownshoe is the answer.

Sell everything and buy CTS-V Wagon. Or on a budget buy a magnum RT.

Have all the things in one car.

In reply to rcutclif:

not a great winter car, see Polestar wagon as alternative. Do the seats in the Chevy SS sedan fold flat? There would certainly be a lot of foam from those kegs