About MS Money Sunset:
It seems that the program has an unhealthy desire to connect to the internet and it seems that the sites it is looking for may not exist and the program can crash -- or get stuck in some sort of infinite do loop. As the only thing I use it for is to keep track of a portfolio, I put the portfolio view in the toolbar shortcuts and that is the only button on the main screen that I select. Everything else is accessed from the portfolio.
The portfolio view can be customized and a column titled "Ann. ret." can be added for each investment. This calculation, best I can tell, is equivalent to XIRR. Included in the calculation are all transactions entered in the selected account for the investment. If you have the same investment in different accounts, the "Ann. ret." column will be different in each. But, if you right click on an investment in any account and select "See analysis" you get the data for all entries for that investment across all accounts.
I'm not positively certain, but I think that MS Money uses the symbol for keeping track of investments, not the investment name. My solution to the question is to always use the symbol for the investment name.
The ability of online quote updates using the yahoo server is available with a little bit of Python knowledge and the scripts from the pocketsense person. As I have a spreadsheet that will download the quotes from the Yahoo server (using a Python script and an excel add-on called xlwings) i have not yet implemented that functionality -- mostly because I'm not a very proficient programmer and also I'm lazy. Programming Python is not as bad as eating liver, but for me, if I don't use a programming language very frequently I have to relearn. It could be said that I don't have 10 years of experience with Python. I have one month of experience about ten times.