I've been 3D printing terrain for just over two years and hear are my thoughts:
I agree with Surv that you don't want to go with a machine off of KS. That made sense 3-4 years ago when things were just getting rolling, but now there are enough companies making solid machines, that there's no reason to take a risk on an unproven machine or company.
My first printer was a Printrbot Simple. While that machine produced good prints, it just wasn't reliable enough and I spent a lot of time repairing it or replacing parts. I would recommend against any of the current Printrbot models. Earlier this year I replaced the Printrbot with a Prusa i3 MkIIs (assembled, not the kit). This is a fabulous machine and has been very reliable and user friendly. I would wholeheartedly recommend one but you need to do your homework to figure out what's right for you. The Prusa, with shipping and customs to the US came to just over $1,000. That's at the high end of what I'd consider an entry level printer.
As to the Kickstarter campaigns or the files themselves. I've participated in a few and I've found them hit and miss. I went in for both the Dragonlock 1 and 2 campaigns and am on the fence for the third (I now have more files than I can possibly ever print). The files FDG puts out are fairly well done with good sculpting and are generally well though out in terms of parts breakdown, avoiding overhangs etc. If anything slips through that is sub par, they've taken feedback quickly and redesigned the parts to address concerns.
I also participated in two of the Printable Scenery campaigns and was much less impressed. For the same price as the FDG KS campaigns you got something like half again or double the amount of files, but they were much poorer in terms of sculpting and there was less though and care taken with parts breakdown. Supposedly they've gotten much better in the last couple of campaigns, but I didn't participate. There's also a ton of other companies crowding in. I've done some of my own design for my own use and it's easy to 3D sculpt and draft something that looks good, but it's slow and hard to design something that prints well every time on every machine with every slicer.
I think with all of the companies selling terrain files, caveat emptor. Renders often look great on the screen but can turn out less great if thought and care hasn't been taken to make sure detail is scaled properly, parts are broken down so they print easily and things like overhangs or bridges are minimized.
My advice would be to find a machine and learn how to print first and worry about the KS campaigns in the future. Most of the successful companies like FDG or PS offer the files from a web store after the campaign, you just end up paying more later. I'd start by just downloading free files from Thingiverse or Yegi and figure out what you're doing before investing any money in files.