Two slightly different animals really so not directly comparable. A Tiger isn't a real off roader despite its pretensions when you look at its weight, gearing etc. but it may give you the adventure buzz and so all is well. I test rode an 800 a few years ago and it was certainly torquey. A very suitable tool for b road ripping about which would be fun chasing others including "sports" bikes. The CRF 300 I would class more of an offroader as in trail riding due to less weight than the Tiger but certainty not a motocrosser where the suspension no doubt would soon let it down. This essentially makes it less ideal on the road. It depends where your personal focus and expected use lies? I don't quite get the title of your post; stupid no, the person who asks no questions when they don't know the answer is the stupid one.
Perhaps you could look at the Kawasaki KLR 650 or a Suzuki DR 650. They will be cheaper than the Tiger and a better touring bike than the Honda CFR. Honestly, the only stupid question is the one you didn’t ask. So please do keep asking for advice on here. Nobody knows everything, we all ask questions. I have been watching a blogger, Marc’s travels on YouTube. He travels on an old Honda Dominator 650. The bike is 32 years old and takes him everywhere he wants to go. Perhaps you could look for something similar?
I bought the previous generation (CRF250L) for my son as a starter bike. I rode a much (much!) earlier generation at university a century ago. The pluses are that the bike is almost bullet proof, lightweight, nimble and you will have no fear taking it anywhere. The downside is the lack of power - the 250 has only 23hp and I think the 300 only has 28hp. This is great as a beginner when you don't want to kill yourself, but the downsides are highway stretches (tedious) and you might soon outgrow the machine (my son is 95kg and the bike struggles uphill). I have seen many reviews saying the 300 suspension is like an old sofa with stuffed up springs. A big drawback is the size of the tank - on the 250 it is only 6,7 litres or about 150km. I think the CRF300L Rally is a better dual purpose/ small "ADV", but you still have to consider the power to weight issue. Itchy Boots has a 300 Rally so check out her YT channel. (PS I have a Tiger 800 XCX and stick to gravel roads, no rough stuff, way too cumbersome).
Look at Itchy Boots videos on YouTube. She is currently riding the Honda 300 through the americas. There is no way she could have taken a Tiger to some of the places she has been - loaded on a canoe for example, it's just too heavy. Also picking the bike up solo in the middle of nowhere is not something that would be much fun with the Tiger. It's horses for courses so the answer to your question depends partly on what you want to do with the bike.
