This time last year, I wrote about two mobile phone features that were "must haves" for me in my next phone: the ability to sync directly to Outlook on my desktop and an SD card expansion slot. The lack of these two features in Windows Phone 7 is what led me to buy an Android phone, specifically the HTC Merge from Verizon - it syncs via USB with my desktop Outlook using HTC Sync and has an SD Card slot.
Since then, I've been tracking the status of these two features at the Windows Phone Feature Suggestion Box at the Uservoice web site. Today Paul Andrew (Admin, Windows Phone) posted in the "SD Card expansion slot should be standard" thread that Microsoft had announced in June on the Windows Phone Blog that Windows Phone 8 supports removable MicroSD cards!
One down - one to go.
I've heard a rumor that the new Windows Phone 8 from Nokia might support Outlook syncing via a USB cable, but I've not been able to confirm this. The thread at Uservoice is still open and taking votes and comments - if you must have it, go vote for it. You can also join the conversation on Facebook in the Windows Phone sync with Outlook via USB group.
Ever since I got my HTC Merge (Android) from Verizon, I have been using HTC Sync to sync my Desktop Outlook Contacts and Calendar and it worked great - when the connection worked. Connecting my phone with a USB cable didn't always launch HTC Sync on my PC. Rebooting my phone and/or rebooting my PC sometimes helped, but the problem continued.
In May 2012, HTC released Version 3.2.20 of HTC Sync. The change log lists Updated USB driver to 3.0.0.021 and Enhanced connection stability among the improvements. I'm not sure which of these fixed the problem, but I've had consistent success connecting and syncing on the first try. If you haven't upgraded yet, I highly recommend it.