Are we still sticking to the 5 grand or less theme? If not, what price point are we going up to?
Just for the sake of updating I have to say you can NOT (usually) get a Nissan Silvia/240sx for non-ripoff prices. Gone are the days of the sub-$5k running S-chassis. These days I would actually argue that you're better off getting either a 350z or an Infiniti g35.
On the flip side, I've seen prices on 3rd gen Supras have actually been going DOWN instead of up. The catch is that they usually have around 200k miles on them. Still, the 7mgte is actually almost as reliable as any other Toyota engine once you do a couple mods to it (head gasket and something else I'm forgetting).
I would replace the WRX with the 2.5RS and/or first gen Impreza since a good WRX for under $5k has gone from being rare to literally impossible. The 2.5RS is also very underrated imho (although possibly a deceptively cheap nightmare) and the 1st gen Impreza is Nissan Sentra levels of being a fun shitbox from what I hear from one of my friends that dailies one.
I don't like the Tiburon (or whatever they call it outside freedomland) but I have to admit its possible to get one for under $5k.
One last thing I can think to add on there is the Toyota MR2 Spyder (aka the 3rd gen, aka the ZZW30). I'm obviously biased since I own one but the prices have been going down to the point where its reasonably possible to get one for 4 grand or less. In addition, they have the Celica GT drive-train so you know they're reliable.
I wouldn't touch the Poor Man's Special section as its still pretty relevant to this day, other than MAYBE replacing the Dodge Neon with 90's Hyundais or any moderately used Suzuki car ever.