2.) The $200k is a little less than 10% of my "Speculative" Funds. I may reduce the allocation down to $100k, depending on what I've determined to be the inherent risk. My questions pertain to that assessment... I'm here to learn from other crypto investors with more experience than myself.
Haha, well congratulations on having $2 million in play money. If you can afford to lose the $200K without it stinging too badly then I guess it might make sense. Thing is, cryptocurrencies tend to be very unpredictable, even the projects that have great teams and seem very promising can go nowhere in the end.
That said, regarding your questions, for an ICO of this size it would be pretty unlikely for it to not end up on an exchange somewhere at some point. Whether that exchange is what you would consider a reputable one is another point entirely, but there will likely be an exchange somewhere for you to switch it to bitcoin which would then be exchangeable more easily to dollars.
However, this will not occur rapidly, because Tezos is an entirely new blockchain, so most exchanges have no experiences with setting up a secure exchange for it. Many other ICOs you'll see the tokens get listed very rapidly, but that's because they're ERC20 tokens that run on Ethereum so for any exchange that already has Ethereum support it's extremely easy for them to add these new tokens as a trading pair. But for a genuinely new project like Tezos it'll take some time for exchanges to get it added, so liquidity will likely be very poor for a long period of time.
The other thing to keep in mind with larger investments is that when the token does get added to an exchange somewhere, it may be an exchange with relatively low withdrawal limits. Some exchanges have ways of doing KYC/AML to increase your withdrawal limits but some are pretty bad about it, and there's really no guarantee that an exchange that will allow high volume withdrawals (in something like bitcoin which you can sell for cash) will support tezos anytime soon. So even if tezos gets listed somewhere and your holdings multiply in value, you may find it difficult to actually exit your position.
Oh and the last thing is? Don't believe most of the stuff you read on forums, do all your own research. People post all sorts of nonsense, whether they're purposely lying for some reason or whether they just believe weird stuff. It's the wild west and you need to do all your research yourself.