In a perfect world, yes the area inside the boot will be dry.
The grease you added will transfer to the opposite side because there is a vent tube connecting the 2 sides, it equalizes the air as one side goes in while the other goes out.
If it's not leaking, and the inner tie rod sockets are tight, just clean away any road grit and replace the boot. Driving it with a bad boot will eventually start it to leaking.
Even if it's starting to leak a little, try some Lucas power steering stop leak. It softens and swells the seals, works very well.
If you plan on keeping the car eventually the rack will need to be replaced. You will get a rebuilt unit complete with inner tie rods. Don't expect high quality, or it to last as long as the original.
When the rack is replaced, the alignment will need to be done unless you DIY and get it as close as you can with the home made toe-in measuring method. Otherwise the shop that does it will say it needs struts and outer tie rod ends and whatever else they can sell, so get ready for a substantial bill!
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Today's Featured Article - Restoration Story: Fordson Major - by Anthony West. George bought his Fordson Major from a an implement sale about 18 years ago for £200.00 (UK). There is no known history regarding its origins or what service it had done, but the following work was undertaken alone to bring it up to show standard. From the engine number, it was found that this Major was produced late 1946. It was almost complete but had various parts that would definitely need replacing.
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