1. I'm not the expert on technical terms.

2. Each bank and brokerage downloads differently into Quicken, sometimes even within the same bank depending on the account. This link didn't work when I just tried it, but I know that with my PNC accounts one checking system allowed automatic downloading, while another required manual downloads (not the individual data, but the files). For each account you need to experiment a little and backup what you have something for which you're satisfied, and start over when you're not satisfied.
http://web.intuit.com/personal/quicken/search.cfm?type=basic...

3. My experience is that Quicken is no faster than a spreadsheet to set up (indeed with all of the diffences between banks, brokerages, etc it may be longer), but MUCH faster and more convenient over time.

4. I've never had problems with downloading various stock, IRA or bank accounts once set up. I have two homes and account for some self-employment through consulting. I don't automatically input Quicken into TurboTax, but the reports make the use of TurboTax relatively simple. I do rentals through a separate account (not a separate data account) and don't use a specialized version (I use Premier). My rental is very simple so yours may be different.

5. I've found Quicken absolutely sucks at options, although others may have found a way to deal with them.

If you can describe the problems you've encountered it may be easier to provide some experience we have. Again, without lots of patience upfront, you won't want to do this. It's somewhat the fault of Quicken but also the fault of many places that don't make access to your data easy.

My opinion, overall, is that Quicken is worth it, for me. I'd hate it just as bad as your setup experience if I had to input what seems to be complicated info into a spreadsheet every week.

Hockeypop