Erekose said:
1. How accurately does it capture the "feel" of Classic Traveller;
Except for chargen, it's almost directly compatible with Classic Traveller. Which is to say, you can mostly use CT worlds and ships with little or no conversion.
The characters end up looking a bit different than CT. They tend to be a bit more broadly competent, and since it taps into the D20 SRD skill set, more areas are addressed.
Since it uses the same experience scale as D&D, and it makes XP a function of the terms you served, characters are a bit closer in capability to one another than in CT. A 1 term character will usually start out at 4th or 5th level, whereas a 5 term character will typically start at 9th level. After that XP is linear, so the level spread between different characters will decrease. I prefer this to the dichotomy that exists in CT.
T20 doesn't penalize you as harshly for age as CT did. If you find players trying to min-max the system and squeeze out the oldest characters they can, you may want to cap terms.
2. How robust is the Traveller d20 ruleset for character interactions, combat, space combat, etc?
Character interaction is comparable to D&D, though the tighter focus on skills will make interaction skills more prevalent than in D&D.
Combat is good. The automatic fire rules are easier to use and more believable than those for many other systems, ESPECIALLY d20 modern (whose autofire rules suck.)
Space Combat in T20 is the best space combat system in a D20 game bar none. It's particularly noteworthy for the fact that it gives all party members a role in space combat, instead of the rest of the group twiddling their thumbs while the pilot and gunner engage in combat.
3. How easy is it to translate experience with D&D3.5E to Traveller T20?
The use the same XP table, but during play, XP expendiatures are linear instead of graded by level. This means that higher level characters/groups will level slower.
4. In addition to the core rulebook are there any additional supplements that you would advocate purchasing (whether rules or adventures)?
The one supplement I absolutely recommend you get is 101 Gunmen (it's at RPGnow/DTRPG under Quiklink).
Gateway to Destiny is a great setting to run the game in if you don't have a CT era sector picked out. GtD features 4 sectors -- an entire domain -- to play in, at the doorsteps of the K'kree and hivers and with a multitude of minor state... a great place to run an interstellar romp.
101 Gunmen is just one of the Traveller's Aides supplement out by QLI. Others are here:
http://enworld.rpgnow.com/index.php?cPath=129_4165&site=enworld
Most of these are vehicle books, though there is one psionics book (I'm not enamored with the T20 Psionics system and use Green Ronin's Psychics Handbook in its stead, so this one is not a big deal for me.)
Of the adventures, I liked the ship-based Epic Adventures (EA#4-6) as well as the odyssey special supplement (that one's hard to find in PDF anymore.) The QLI page at the ENWorld RPGnow shop is here; take a look around:
http://enworld.rpgnow.com/index.php?cPath=129
Other than QLI, Comstar/Avenger have a few titles nominally set in the Gateway domain (though not using T20). They had an adventure called Homecoming, but it appears to have disappeared.

Their Short Adventures supplement is a good one, though. Check out their whole selection, here:
http://enworld.rpgnow.com/index.php?cPath=1542