Sounds like a hell of an adventure! Any pics of youre trip??I disagree with a lot of stuff mentioned on this site and wonder how many of you have actually rode the bikes you speak of?
I agree with those that say 2-strokes are cheaper to buy, cheaper to maintain in the long run, and better resale value. A newer 250 have TONS of torque and more then ample power. Any more and you face the wear down effect of unnecessary power (Ie, 450's and 300 2t)
That being said many like 4-strokes for their electric start (trail and some MX versions), added traction, and ease of throttle control. The downside is their weight which is fine when riding, but you tend to suffer from it when wrestling the bike.
There's a time and place for all bikes. While speaking about bikes I'm talking trail riding, mostly gnarly, technical trail riding. Many (almost most) serious riders ride two strokes because they know the benefit and more interested in riding 3-4 hours non-stop without fatigue. They also know how to caress the quick power of a 2-stroke to their benefit. Modern 2-strokes don't have the "powerband" the old bikes did. Powervalves have changed all that and they have great torque with a cross-over point where the valve opens and HP kicks in. It's not like riding a 90's 2-smoke.
That being said, 4strokes have come a long way as well. They now start for starters.. har har. EFI and many having happy buttons make them a pleasure to ride. They are fun and easy to ride which is what sells them. One thing to keep in mind is power is not everything. A 250F ridden by a competent rider will still be wicked fast and probably have more fun then on a 450. I always enjoy riding 250F's, but at times I can see the power being an issue only when getting caught in the wrong gear, and having to gear change a lot more. There's something wicked fun about riding one all WOT and careless and still being in control though. It brings a smile to my face at least. The engine braking and reasonably quick handling make it a nice change from my two strokes until I have to wrestle or fight the bike.
If you look 2stroke, look at only the newer ones. Same with 4-strokes. For 2-stroke the 00+ CR's were torquey and a trail favourite, same with ~03+ YZ250's. RM's seem to lack a bit of torque (I owned an 04 too), and KTM don't bother unless it's 08+. The newer handling is well worth the extra money. (I also owned an 08 KTMXC).
Older 4-strokes can be money pits. 05/06 down were often bad at overheating and poor at starting. 07+ were much better in that regard.
Here's another MASSIVELY important point. DO NOT BUY A MX BIKE FOR TRAIL USE! Sure, it can be done but you'll hate yourself. 18" tires, different gear sets, happy button, power characteristics, etc massively change the way a bike works on a trail. If you are going to mostly ride trail, or even 50/50 I'd still go trail bike. Stiffer springs and dampening can be changed for the odd, non-competitive track day. A track bike can't be made a good trail bike without a ton of work. They are often cheaper then a trail bike with good local trails for a reason. Nobody wants them.
Good luck with the hunt. If I were looking (and I somewhat am) I'd consider a GasGas for their quality ride and cheap resale (smaller seating ergonomics though), same with Husqvarna. Also, "older" KTM's because of the KTM bandwagoneers. 08-10's can be had for a much more reasonable cost now and they are good bikes for the most part.
For 4-strokes, Husaberg's are dirt cheap used (and very expensive new). Just watch out for the FI problems. WR's and CRF-X's have always been a solid bet but some of the KTM specific trail bikes were good too. The 450 and 530's being street legal as well in certain packages/years. Probably best to avoid the Kawasaki, Suzuki, etc if you want to sell the bike for more then a few pennies, although I've been dieing to try the RMZ450.
The bike I have now? 03' Honda XR650R. Besides the gearing it's a hoot of a bike. I've rode it now 20,000km in foreign countries in the last year - 4,000 KM of Baja in Feb, and just finished a solo 16,000KM trip from Moab, Baja, Mexico, Belize, Guatemala, Mexico, and back to Phoenix. It really shows what's important. It's not about being the fastest, not the newest, absolutely not the coolest or best looking, its about having fun. The XRR is a wicked fun bike. I can keep up or be faster then most of my buddies on moderate trails but I can also take it on dual sport trips where we camp every night on mountains, etc. That being said I'm missing the gnarly technical rides I enjoy and will be buying a used bike again this year.
Good luck and have fun!
(Also stay on designated trails, don't abuse the environment, and be responsbile. Pack out your garbage)