01-30-2014, 04:48 PM
20+ year Quicken user here. I gave up on Quicken for MacOS about 6 years ago and now I use Quicken 2011 through win7 on a VM. Being able to download all transactions like credit card statements, brokerage accounts, etc has been a godsend. I'm not sure if you can do that with the OSX version, but it's very robust on the windows side either with Quick Connect or QIF files.
I can't believe I used to do credit card transactions by hand for the first 10 or so years (yes, I'm that exciting to talk to at dinner parties). Back then I would separate things into discretionary and non-discretionary and call it a day. It didn't give me much granularity, but it was useful to know how much I was spending on needs vs wants. It gets tricky when I would buy higher quality food and booze at the grocery store for entertaining. Even now that I can download transactions and 95% of my purchases are from the same vendors, I try to keep it simple. For instance, I lump water, gas, electricity into the same "utility" category but separate from telephone, cell, internet and satellite; the first one I could never really eliminate and the second one I could easily cut back on if needed. Likewise, Costco, TJs, Kroger and Whole Foods are all the same "grocery" even though I might by a 6-pack of surfboards at Costco. The upshot: Fewer categories is definitely easier but gives you less granularity. It's definitely a balance. Any, I've digressed. Again.
If I didn't have the ability to download and was dealing with several investment accounts, I'd probably manually update them every quarter or monthly at most. I agree that it is a pain with a lot of employer sponsored retirement accounts because many of them, say, take fees in the form of mutual fund shares. Reconciling that can be tedious. Monthly or quarterly (or even annually) is good enough because when you start to look at year-over-year or decade trends, you shouldn't care about what happens day-to-day. You really don't need to worry about tracking in retirement accounts since all that will be taxed as ordinary income. If it's a real PITA, just track the balance each quarter and not the investments inside (but do keep track of your and your employer's contributions). That's more than 80% of the population would do and in the end I don't really care how a mutual fund performed over the last 14 years.
If you are dealing with taxable brokerage accounts, then you definitely need to be diligent about capturing all the data since your gains or losses are based on the cost basis of each lot.
Whatever you do, just make sure you stick with it and it's easy enough to explain to someone else. That's how I figure if my system is too complicated; if I can't explain it to a 10-year old kid, I'm surely going to forget how I did it myself in 6 months!
I can't believe I used to do credit card transactions by hand for the first 10 or so years (yes, I'm that exciting to talk to at dinner parties). Back then I would separate things into discretionary and non-discretionary and call it a day. It didn't give me much granularity, but it was useful to know how much I was spending on needs vs wants. It gets tricky when I would buy higher quality food and booze at the grocery store for entertaining. Even now that I can download transactions and 95% of my purchases are from the same vendors, I try to keep it simple. For instance, I lump water, gas, electricity into the same "utility" category but separate from telephone, cell, internet and satellite; the first one I could never really eliminate and the second one I could easily cut back on if needed. Likewise, Costco, TJs, Kroger and Whole Foods are all the same "grocery" even though I might by a 6-pack of surfboards at Costco. The upshot: Fewer categories is definitely easier but gives you less granularity. It's definitely a balance. Any, I've digressed. Again.
If I didn't have the ability to download and was dealing with several investment accounts, I'd probably manually update them every quarter or monthly at most. I agree that it is a pain with a lot of employer sponsored retirement accounts because many of them, say, take fees in the form of mutual fund shares. Reconciling that can be tedious. Monthly or quarterly (or even annually) is good enough because when you start to look at year-over-year or decade trends, you shouldn't care about what happens day-to-day. You really don't need to worry about tracking in retirement accounts since all that will be taxed as ordinary income. If it's a real PITA, just track the balance each quarter and not the investments inside (but do keep track of your and your employer's contributions). That's more than 80% of the population would do and in the end I don't really care how a mutual fund performed over the last 14 years.
If you are dealing with taxable brokerage accounts, then you definitely need to be diligent about capturing all the data since your gains or losses are based on the cost basis of each lot.
Whatever you do, just make sure you stick with it and it's easy enough to explain to someone else. That's how I figure if my system is too complicated; if I can't explain it to a 10-year old kid, I'm surely going to forget how I did it myself in 6 months!