I'm kinda lost on what to do to replace the Yamaha as I'm fairly certain its not going to be recovered.
option 1 - find a cheap truck or van (preferably 4wd), use the rest to buy a used dirt bike (thinking a KDX220 or XR400) and plate it for local trips and messing around the woods, start messing around with hare scrambles and/or enduros too.
option 2 - find a $3000-4000 car, setup for autocross already (there's a couple ES MR2's available right now, as well as a few ST civics and STS miata's and crx's...). Or cheap truck/van + kart and go racing.
option 3 - buy a more road oriented bike and continue along w/o a car. Stay home if the forecast is even remotely predicting frozen precipitation. There's a few bikes I've been somewhat interested in, but nothing I'm particularly enthralled with. Short list includes the 883 Iron, maybe a DR650 or KLR, an older VFR, F800GS, older GS BMW's, etc sport tourer, or possibly an older sport bike.
option 4 - Find another WR250R and continue along w/o a car. I really loved that bike and want it back. I might be able to find one used with the same aftermarket stuff as mine had for what I get for mine from insurance. Still no car with this option.
My commute's about 20 miles into Baltimore 3-4 days a week, and where I work motorcycles park for free and I can find a spot anywhere w/o a problem. I usually ride to campus as again its MUCH easier to park a motorcycle in the designated areas right by the entrance to the buildings my classes are in, and the parking permit is cheaper by half, but there is a campus shuttle that stops at my complex. My apartment complex only gives us 1 space for 2 cars, so with a car I'd have to always fight for a visitor spot, a bike fits nicely in front of my roommates truck in our spot. I do have a place to put a dirt bike and/or a kart.
I'd like to get back into racing somehow regardless. I'd either get a stock class car that someone is selling to move up, try to build a LO206 briggs kart for w2w racing, or build an f125 kart for autocross. I could get by with a plated dirt bike on the local DS rides I do, but would probably not be able to take the longer trips that I'd really also like to keep doing w/o trailering. Considering most of the trips I do are pavement or soft-roading, a street bike would probably work just as well and be more comfortable on the pavement and high speed stuff, but more hell in the dirt, tire selection will be key of course. And I could always just stay the course and get another WR250R. It did just about everything I wanted a motorcycle to do except make my eyes bleed with acceleration without complaint, and I'm having trouble thinking of a car, truck, or bike that I'd rather have instead of it.