Remember the speed of your DSL or Cable is going to be your bottle neck...if you are getting 5-10mb from your broadband having theoretical speeds of 50mb to 1000mb up to your DSL router makes little difference. However if you are wanting to transfer data between computers in the main house and the sleep out that is a different story.
Also good to remember that 802.11n wireless has a longer range than 802.11g. Do you know what the previous folks had? If they were having drop outs using 'n' running wiring may be the best option, if they only had 'g', maybe you don't need to run any wire - being that wireless is so susceptible to your local environment I would suggest testing the range by putting your Apple in the house and checking what it's signal is like out to the sleep out. Once you know that you can figure out if you need to buy a different base station with better range, run a wire, etc.
I love the Apple gear as the software does a good job of configuring itself for dual routers etc. Going forward there is no need to replace the Express as it will either be used solely or in addition to a base station, and obviously good for streaming music to your stereo. I'm not sure of the benefit of extending your wireless network in this instance though since if you have range from the house to the granny flat why would you need to extend it further than that? However if you need to wire it to get the signal there, then you certainly will need two devices.
Buying two standard routers gets tricky as you then have multiple DHCP servers that may conflict by default. You can make them work but the simplest, although pricey, option is to buy an Apple Extreme base station to work with your Express. Look for refurb kit from the Apple store if you go that way to save some $.
There are so many options with how you can set this up so if you still are stuck after the collective wisdom of KB's kicks in feel free to drop me a PM.
"And if I claim to be a wise man, It surely means that I don't know"
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