I'll preface this saying I have been searching and reading around the forums a lot over the past several weeks. Some of this is me just wanting to put some thoughts and notes down. Feedback and discussion around it is a welcome bonus too. 
Currently I have a '13 Tacoma Double Cab. Our youngest of 3 kids is 3 now. It's been challenging working around it but also with more reduced driving the last few years didn't feel a huge need to go buy a vehicle during the height of market craze. The oldest is about the size of a small adult so we have managed pretty well with the 4 of us. When all 5 have needed to take the Tacoma, it's painful before we ever leave. Immediately prior to the Tacoma, I had an '03 4Runner v8 RWD for about 5 years and have owned a Toyota for most of the past 20 years. Loved that 4Runner but the lack of 4WD did show up a few times to bite me. I don't have any big off-roading needs but it's nice to not get stuck even in mild conditions. It was a compromise made when we bought it and just couldn't hold out to find one in the budget with 4WD. Even before the last kid expansion I had looked at mostly European crossovers and that started when VW had the TDI fix. Did like the 958 Cayenne and the late first gen Q7s, but ultimately was scared away from all the TDI problems I read about. The gas engine options in each were also nice, but also not vehicles I wanted to really be able to hold onto long term. Came close particularly on one of each that the deals just didn't work out.
Few weeks ago I really started considering finding a 100 or 200 Series. I do find it would be easily possible to get a cheaper, earlier model while keeping the Tacoma. It's not really until the mid-years of the 200 Series that I think it would make sense to part with the Tacoma right away. The early 200 Series are priced pretty evenly with late 100 Series. I do have a higher comfort level with the 4.7 and perhaps a bit less of the electronics and other high-cost systems. Though a lot of the research leads me to the fact that the newer ones are going to behave and feel more comfortable on road. Considering what other vehicles I was looking at and knowing they were also going to have some higher maintence and replacement costs, I am ok with that. I'm not really considering a 5th gen 4Runner as don't care too much for the design and interior of them. Finding a v8 4WD 4th gen that is an overall good vehicle also seems to be a bit more of a needle in a haystack these days and comparable in prices with other options while maintaining some of the quirks and shortcomings.
Hoping to be able to find a few different models to test drive and take an in-person look at soon to really get a feel of each.

Currently I have a '13 Tacoma Double Cab. Our youngest of 3 kids is 3 now. It's been challenging working around it but also with more reduced driving the last few years didn't feel a huge need to go buy a vehicle during the height of market craze. The oldest is about the size of a small adult so we have managed pretty well with the 4 of us. When all 5 have needed to take the Tacoma, it's painful before we ever leave. Immediately prior to the Tacoma, I had an '03 4Runner v8 RWD for about 5 years and have owned a Toyota for most of the past 20 years. Loved that 4Runner but the lack of 4WD did show up a few times to bite me. I don't have any big off-roading needs but it's nice to not get stuck even in mild conditions. It was a compromise made when we bought it and just couldn't hold out to find one in the budget with 4WD. Even before the last kid expansion I had looked at mostly European crossovers and that started when VW had the TDI fix. Did like the 958 Cayenne and the late first gen Q7s, but ultimately was scared away from all the TDI problems I read about. The gas engine options in each were also nice, but also not vehicles I wanted to really be able to hold onto long term. Came close particularly on one of each that the deals just didn't work out.
Few weeks ago I really started considering finding a 100 or 200 Series. I do find it would be easily possible to get a cheaper, earlier model while keeping the Tacoma. It's not really until the mid-years of the 200 Series that I think it would make sense to part with the Tacoma right away. The early 200 Series are priced pretty evenly with late 100 Series. I do have a higher comfort level with the 4.7 and perhaps a bit less of the electronics and other high-cost systems. Though a lot of the research leads me to the fact that the newer ones are going to behave and feel more comfortable on road. Considering what other vehicles I was looking at and knowing they were also going to have some higher maintence and replacement costs, I am ok with that. I'm not really considering a 5th gen 4Runner as don't care too much for the design and interior of them. Finding a v8 4WD 4th gen that is an overall good vehicle also seems to be a bit more of a needle in a haystack these days and comparable in prices with other options while maintaining some of the quirks and shortcomings.
Hoping to be able to find a few different models to test drive and take an in-person look at soon to really get a feel of each.