Here's my 2 cents. I've owned two 3rd gens and one 4th gen. My first was a 99 with the 3.4 auto. My second and currently still in the fleet is a 99 with a 2.7 manual. I had pretty big plans to keep it as a pavement queen including adding a turbo but I started to see some limitations in the past few years. I even had 01 sport interior parts to swap into the car but never got around to doing it. Here are my pros / cons with 3rd gen ownership (may be a reiteration of what some others have said on the thread).
Pros:
- felt more connected and mechanical in driving
- simpler maintenance (IE brake master cylinder doesn't include replacing the entire ABS unit)
- less electronic nannies (TCS / VCS)
- the handling on mine felt more like a rwd car (maybe partly because its lighter and was only 2wd) - similar to comparing my FD to my former RS4
- dual auto front window down function
- availability of 5 speed manual
- aftermarket parts availability
Cons:
- some what dated controls / interior ergonomics
- lack of power (felt this more in my 3.4 than the 2.7 mainly because of the manual, but I still felt the limitations of the 4 cylinder for sure) availability of boosting options helps here though
- uncomfortable seats for long trips
- not much else to dislike - just the usual older car stuff
I was up and down between getting a 5th and 4th gen around this time in 2017. I got some good time driving my friends 5th gen limited with full time 4wd. I test drove one beat up 06 V8 4wd from a local used car lot and decided that I needed to find a 4th gen V8 for sure. Between the two generations, I felt they handled pretty much the same. The 5th gen My decision to even contemplate buying a non-3rd gen was shocking to me but mainly I wanted something a bit larger to transport my dogs around. If were just me, I would have continued rolling along with the 3rd gen. I've always been a die hard 3rd gen fan, thats why I bought a second one to finish the project I never finished.
Anyway, I bought my 4th gen sight unseen and flew into Philly 6 weeks after buying to pick her up. I pretty much changed my mind instantly after I drove her off the lot. At 143k miles, she felt like she had only done like 30k. Even the tired XREAS made the truck feel pretty plush for the entire 1000 mile road trip back home. Here are some pros / cons to the 4th gen from me.
Pros:
- V8 availability (I'm not going into a debate but I did mainly pick the 4th gen for this reason)
- interior is very similar to the early 5th gen (2010-2013) - so it feels not as old especially with an updated carplay / android auto unit
- seat comfort on long trips (I used to get back aches in the 3rd gen, I don't get them in the 4th gen)
- rear seats fold without needing to remove the head rest (its the little things)
- extra storage compartments in rear wheel well
- electronic closing rear hatch (not auto close but you don't have to slam it to close the rear hatch)
- XREAS is comfortable (although I ditched this already and it still feels pretty decent with the aftermarket setup)
Cons:
- size (it feels much bigger than my 3rd gen and makes my 3rd gen feel like a sports car) - although it also has a larger cabin
- handling (handles like an AWD vehicle with more understeer feel vs my 3rd gen / also feels less connected to the road)
- V8 timing belt (2.7 on 3rd gen and the 1GR has timing chains so this is a V8 specific item) - I don't see it as a con because most cars have this as a maintenance item
- front calipers prone to freezing (my passenger front was frozen) - I fixed this by going with an aftermarket BBK though (not a route everyone is willing to go with but with the amount of money being thrown around for suspension and engine upgrades, I figured its worth the investment and time. Time is golden for me, service it once vs having to replace frozen calipers every few years)
- complexity for maintenance (more sensors / solenoids that can go bad over time) - IE: secondary air injection pump issue (v8 specific), 4wd lo solenoid
- add on of VCS, TCS systems (just modernization I guess) - at least you can turn them off without some silly pedal dance process like the FT86/BRZ
After I came home with my 4th gen, I still drove my 3rd gen on and off for 2 months after I got the 4th gen but after I got it registered, the 3rd gen has pretty much sat in place since late March of this year. I only drive it once every few weeks to keep the parts moving. I'd keep it as a fun car, but 5 vehicles for one person is just too much. I love my V8 4th gen and have almost jumped at the opportunity to pick up a lower mileage one several times, but for now I'll save my monies and continue to enjoy the one I have. I know if anything happened I'll get another one for sure. It fulfills all the check boxes the 3rd gen does and more. Those are my 2 cents as far as daily drivability.