I Have No Idea

Bolded that. I think that's rather...I don't wish to say naive, but at the very least certainly not the case. Look, you come from the exact same intellectual background as me just across the river. I'm pretty sure you must have seen awesome students/early career people go away and idiots promoted based on things other than academic merit. My own professors have been quite open about it. Even as undergrads, we were hardly stupid and it was quite obvious. I dare say there have been several excellent people drop out over the years, but we just didn't realise it. Often  I see some name on an amazing published thesis only to be unable to find said author anywhere in academia.
 
There aren't enough positions, the positions that exist are hardly given solely on merit, even those positions are rarely long term nowadays. I was told to think of it thus: Go in for love of the subject and try your abject best but don't be too shocked if it doesn't work out. Such thinking seems to have the right of it as far as I'm concerned.
 
The alternative is to believe that the only good Classicists come from a handful of departments working under a small group of people who happen to know one another with a few outliers here and there. 

Lead me not into temptation. For I will write it. 

Does it matter what language? Erm one of the pitfalls/great things about Classical pedagogy is that people go directly into the highest register of awesome as hell literature. Like...learning English and then given anything from Beowulf to Shakespeare to read. I find it hard to gauge difficulty now, I don't really have trouble besides contested passages and I already spoke Greek before learning ancient Greek, but I have some observations from teaching.
 
Firstly, the traditional starters are tradition for a reason. Caesar for Latin, Xenophon or Plato for Greek. These make sense and working through these will give you a solid grounding in either language, that being said there is a case for certain non standard choices: Chariton's Callirhoe is an excellent choice, its very manageable Greek and repeats a lot of vocabulary. Very simple syntax and not too many varied forms or idioms. However it's not strictly classical Greek and a decent proportion of the vocab you learn will be useless due to the emphasis on piracy, tomb robbing and so on. 
 
In fact, as long as you keep in mind it's not quite classical, any of the novels will be fine and these are all accessible without too many genre conventions affecting language. 
 
Latin, well a lot of people seem to vary from omg I want to start with Ciceronian Latin to I'll read the Res Gestae Romanorum. The latter is an increasingly popular choice but...its too simple, to non Roman in Latin usage...too...its just not a very sensible choice and if you want something late some section of Ammianus Marcellinus re very, very, manageable indeed but there are certain genre conventions (history) which do have an effect on the difficulty of the language. Its much easier than Tacitus, Cicero etc though. Eutropius is also somewhat easy. He was actually used as a sort of textbook in late Roman schools too.
 
What it comes down too though, is that it doesn't matter. There are so many graded readers, commentaries etc out there to help. Just pick something. Whatever you choice you can triumph via hard work. 

I have not heard that the IFA has had problems funding its PhD students, although I do have friends in their MA program who did not receive funding. Everyone whom I know who is in their PhD program has full funding.

Professor Chiu at UVM is an incredible mentor, scholar, and teacher -- and has an incredible sense of humor to boot.  Ever heard of Classics Ryan Gosling? She's the mastermind behind it. 
http://classicsryangosling.tumblr.com

Sometimes, I feel like I am the King of Foot in Mouth moments, especially around professors or people I want to impress. I think I (sub)consciously overcompensate for my inhibitions by saying inappropriately uninhibited things that aren't event totally true.... if that makes any sense.

Tonight, at a small departmental get together:

Professor / Also Dept Chair: Well it takes so long to read every word of those articles!
Me: Every word! Ha! I barely read the abstract and then skip all the numbers and charts and graphs and then just pretend I've read it when I'm in your class! I've hated all the readings! ha ha ha!
Professor: 
Me: 
 
 
I suffer from things like this all. the. time. I'm usually able to shrug and laugh it off, but sometimes I can't believe the things I hear myself say.
 
Anyone have similar experiences? What have been some of the best/worst/funniest? How have you recovered, if at all?