A Terminal Server is only necessary if both office locations are open simultaneously. There's no need to buy a terminal server if only one office is open at a time.
A few things might make things easier. 1. How many users do you have? 2. How many people are at each office at a time? 3. Do you have an existing server?
To make things simpler. Microsoft Offers preconfigured solutions for both roles. You can get SBS 2011 Essentials ($400) and MultiPoint Server 2011 ($450) + CAL Cost for each.
Server 2012 has also hit the market and can be configured manually. You would only need to buy that for $810 plus the price per RDP CAL. But you are likely going to pay a lot for the configuration.
IMO Option 1 would be much better depending on your tech level. I would also advise virtualizing this on one box to save some money as well as simplify management.
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