Hi Ted,
Thanks for your interest in Fund Manager.
You're right, all Fund Manager versions can do #2.
The answer to #1 is not so straight-forward. There are several different ways you can get your distributions into Fund Manager. The best method depends on your situation:
1) Retrieve from your broker. This is by far the easiest method. A potential problem in your case is the length of time you are looking at. Most brokers don't keep 10 year's worth of transaction data available on their OFX server. For more on this feature (available in all versions of Fund Manager), please read:
http://www.fundmanagersoftware.com/tintrtv.html
2) Import your distribution (and/or other transaction) data from a file. If you have your distributions in any electronic format now, you can most likely import them into Fund Manager. You can use the "Generic (.CSV or .TXT)", "Quicken Interchange Format (.QIF)", or "Open Financial Exchange (.QFX or .OFX)" formats in all versions of Fund Manager.
3) Retrieve historical dividend data from Yahoo (Historical). The Professional and Advisor versions of Fund Manager can retrieve the dividend data available on Yahoo for a variety of stocks and mutual funds. A potential drawback of this approach is when Yahoo doesn't have all the distribution data available for a particular stock or mutual fund you own. You can evaluate this by browsing to Yahoo Finance (finance.yahoo.com) and looking up the quotes for the securities you have owned. Click on "Historical Prices" on the left side, and then choose the option for "Dividends Only".
4) Of course you can also manually enter any distribution data. You may also edit/add/delete any data imported/retrieved with any of the methods above.
You can download and try out any version of Fund Manager before making any purchase decision. All of the trial versions are fully functional, but limited to 60 starts.