Okay, so this is a touch nitpicky or it explains things better. Obi-wan, at the end of Sith, returns to Tatooine to deliver Luke to the Lars family. Alrighty. Got ya.

How did he get there?

If he flew on his own wouldn't he have his own ship and, thus, in A New Hope, already have a ship to fly off the planet with Luke? He was a good pilot (even if you take into account that he doesn't much like it). Surely he could have flown off the planet himself with no need of Solo or the Falcon.

If the ship was damaged over time would there not be a place to repair it or even keep it fixed up over the years (ala a place like Watto's)?

If he did not fly there then was he dropped off by the Tantum (sp?) and Bail. If so, this makes it more clear how Bail knew where Obi-wan would be when he tells Liea.

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This also begs the question: Was Yoda dropped off on Dagoba first? If so, Luke was with Ben. In Empire there are two lines that have always stuck with me:
1) Luke says that being on Dagoba was "something out of a dream"
2) Later he says that "there's something familier about this place. I don't know...I feel like..."

..he's been there before? If so, when? Why is the place familier?

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I like to think that: Obi-wan, Yoda, Luke were flown first to Dagoba where Yoda was dropped off. Goodbyes were said. Luke experiences some memory of the place. Obi-wan knows exactly where Yoda is to send Luke there in Empire. Obi-wan is then dropped off on Tatooine and Bail knows where Ben is when he tells Leia.

If that is Lucas' intent, it all ties in nicely, me'thinks.

He was just dropped there. He didn't have a ship which is probably why they needed the Falcon in ANH. I don't think it was important to show a small detail like this. I can't speak about Yoda going to dago as I have not seen the digital version yet.

Well, any thoughts on why Luke might find Dagoba familier?

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I haven't seen the digital version as of yet, either. Isn't he just there in that version? Anyone who can elaborate it would be appreciated.

Good question. If anyone has viewed the digital print I'd be interested in how it went down. If the entire group stopped on Dagobah before dropping Ob-wan off then Luke may have been on the planet for some time.

Then again, perhaps he saw it through the force, like he did with Cloud City.

" ... like something out of a dream"

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I could buy that he felt Dagobah because of Yoda's watchful "eye" on him (as Yoda admits to have been watching Luke since he was born) but I do enjoy thinking that he was actually on the planet for a short time as an infant. Seeing Yoda lad on Dagobah alone won't ruin anything for me but if he does land alone I'd much rather it be left open to my above notions.

Another option for the "what happened to Obi-Wan's ship" question could be that when he landed at Mos Eisley, he sold the ship (since he figured he wouldn't be needing it any more), and used the money to buy the eopie, and probably still had enough left to buy his new "home" .

There are many ways these questions could be explained, and any number of the exlanations work fine for me.

See ... this is what happens the one time that Lucas does not show a ship taking off/landing ....