Been a while; I think I have older threads summarizing the Tundra.
in 2007 they did an overhaul, and made what you can buy today. In 2014 they did a gen 2.5--it's new sheetmetal, new interior--but same drivetrain. Hence the point 5 designation. Pre 2007 was a different, smaller beast which I'm guessing you don't want.
I'm assuming you don't want V6 (I wouldn't). 2007-2009 had the 4.7L V8, good motor if not a bit low on power. Timing belt and 5 speed automatic are drawbacks. 2010+ use 4.6L for a base motor; pinch more power but more importantly a six speed auto, which bumped mpg. And gained a timing chain. 2007+ have the 5.7L for the top engine. The 4.6/5.7 can have issues with water pumps; air injection pumps are a big issue, or at least used to be (and they ain't cheap). Front differential was a problem too, although they all should have been fixed by now (bad bearing preload, so it was only a few years, but my 2010 was bit by it, around 80kmiles). Transmission is a "sealed" unit but did a fluid change and it wasn't that bad, IMO. And it's an Aisin unit, and Aisin is usually good.
If you do get the 4.6, do yourself a favor and get the towing package. It comes with slightly deeper gearing, which the 4.6 needs. But do yourself a bigger favor and get the 5.7. I've never driven one, largely because I don't want to depress myself as to what I'm missing.
Personally I'm ok with the rest of my truck. I have a 2010 so it's pre the redo; and I like it that way. I've got the bench seat up front, plain gray cloth interior, column shifter. 4 doors and a 6.5' bed. Works for me, but I suspect adults won't like the back seat that much (my kids are small enough that they don't care). That said, I doubt anyone else would like it. The TPMS system is stupid; it just lights up the dash if a sensor is off. No individual tire read out. No DIC to tell you exact engine temp etc (I don't even have the mpg readout, but it was an option on the higher trims). Towing capacity may be decent but payload is low. VSC/TC is awful, it takes nothing to engage and cut power--it's the first thing I turn off if I'm driving in snow. As a result it desperately needs snow tires in snow. I don't have a backup camera but I believe that is standard now. mpg... let's not discuss that, eh? it may be a truck but last I knew Tundra trailed the pack in unloaded mpg (loaded they all seem to head to the same single digits).
I picked my 2011 up in 2013 with 50,000 miles for $25K. 
