2nd Gen Regular Cab vs 3rd Gen Access Cab

I'm looking for some advice. I've been lurking the forums for a couple of years and the search function has done me well so I haven't posted anything. I apologize in advance if this is posted incorrectly or in the wrong location.

Lately I've had some issues with my truck and am contemplating trading it in on a 2022 TRD Sport Access Cab. I bought my 2008 Reg Cab a little over a year ago with 89k and it has been generally reliable, but these past few weeks have been rough. 3 weeks or so ago my front diff actuator failed so I replaced that (apparently not uncommon), then last Friday when starting it a power steering line blew so I replaced both the pressure and return line (it was -20F and I was on my way to work). I need reliable transportation for my 35 mile commute but absolutely love this truck. I'm thinking it may be time to get into a newer vehicle but I'm not sure. Has anyone traded up to a 3rd gen from a 2nd gen and regretted it? The pros are that I could move up to a v6, get a back seat, and have a much cleaner truck moving forward. The cons are the cost obviously and the appeal of the regular cab (short wheelbase, great on gas, by sticking with this truck I'd be able to mod it sooner rather than waiting with a new truck)

If I hang onto this truck I'll likely start dumping money into it over the summer to make it more reliable and pleasant to work on in the future (upper/lower control arms, ball joints, inner outer tie rods, steering rack, sandblast/wire wheel and paint axle, basically everything under the truck that's rusty). It got a new frame before I took ownership but a lot of the stuff bolted to the new frame looks like it also should've been replaced. I also bought it with the body damage, it doesn't bother me much and I know the bedsides bolt on and off so I look for silver ones every now and then but am not willing to invest in buying and painting one.

Sorry to drag this out, I'm looking for opinions from some more experienced Tacoma owners. Should I restore/upgrade the 2nd gen or trade it in for a 3rd gen?

A few pictures of my truck




The truck I'd trade it in on

 

I vote for the newer truck. Less things to worry about for a long time. Fresh start for the new year...





Any hoo, choose what best for your situation...

 

I have the 2020 version of that exact truck with a 6 speed and love it! Noone can make the decision for you, but you won't be disappointed in the new one. I would recommend the KD Maxx tune if you do get it though. Makes a world if difference.

 

Things to ponder:
I reluctantly let go of my '06 TRD OR AC after 15 years and 127K miles. I loved the truck and its 6 speed manual with a strong 4.0 V6. The frame had been replace by Toyota after about 9 years on New England roads, so that particular issue was no longer a concern. However, every time I brought it to my local shop to do the seasonal tire swap (snows on steelies to warmer weather on alloys) I noticed how corrosion was beginning to take a toll on much of the undercarriage. This makes repair/replacement of some components difficult, if not impossible. While repairing and maintaining can be reasonably economical, it can also be a royal PITA.
The tipping point came as I began to realize that wifey and I would soon be completely on fixed incomes and obtaining financing might become a challenge. In addition, due to the evolution of my lifestyle I figure it was time to accept that an automatic tranny might be better. I have no great visions of a Taco "build". My mods will be simple, reversible, and primarily aesthetic.
When comparing the 2 versions, I find that the 3.5V6 has nowhere near low end torque that the 4.0V6 offers. I could often start out in 2nd gear in my '06. Then there's the getting used to the alleged 'gear hunting' of the 3rd gen. It does shift much more than I would have had to in my 2nd gen manual. But then one has to understand the higher RPM power band of the 3rd gen 3.5V6. It's a matter of understanding this phenomena and both me getting used to the auto AND the auto learning my driving style. We both had a learning curve. I have adapted.
My '21 TRD OR AC tows my trailer with a 1-ton subcompact tractor just fine. That's about the hardest it'll ever have to work. I do occasionally get off the paved roads with it, but nowhere near many of the off-roaders you'll see here on TW. Fuel economy is pretty much the same as my '06 was - currently averaging 18 MPG over the almost 13K miles that it's been driven. Both trucks had/have a Leer 180 cap so I can carry 'stuff' in the back out of the weather.
Bottom line: I don't regret the change. Can't say that I would rave about how great it is, but I'm satisfied and won't look back.
YMMV.
EDIT:
My 2006 TRD OR AC:


My 2021 TRD OR AC:

 

I had an '05 w/5sp. If the frame is good, I would keep what you have. Use that money for something else.

 

How about getting a cheap commuter car and keeping/improving the truck?
You could get a 5 year old Corolla/Yaris/Camry with good miles for less than 1/3 of a new truck.
Car would get almost 2X the fuel mileage too.

 

@RustyGreen the truck already was my secondary car. I also have a Miata with a decent amount done to it and more to come. I like having a truck for occasionally towing/hauling stuff and I ski so a Tacoma is great for getting to the mountains.

 

FWIW: I was just in a similar situation recently. I just recently accepted a job that involves a 45min commute and needed something more reliable. Granted, I haven't had any problems with my '14 AC TRD OR yet or my '10 Mazda 3 Sport, but I felt like it was going to happen soon. Like you, I absolutely love my truck and knew that I would really regret getting rid of it. I've also driven several 3rd Gens and can't see spending that kind of money, with the way the market is today, on a truck that I don't love. I ended up trading my Mazda in for a 2022 Hyundai Ioniq Hybrid. I can't see ever getting rid of my Taco; I've put too much into it and don't think I'd ever get what I feel it's worth in trade. My Mazda was a blast to drive compared to the Taco, but I'd rather have the versatility of the truck than the go-cart handling of my Mazda. The Ioniq is, by no means, exciting. At 55-60MPG though, it'll do.