Analysing your own portfolio/investments

Like many of us I guess, I am sort of playing my own Private Banker by managing my own investments, but I am currently not satisfied with my own service level. I found that I have the habit of not doing too much with own investments, partially because of a bit of a perfectionist "do-it-properly-or-don't-do-it-at-all"-syndrome: I feel that it's too much effort to do it properly, so I often decide to leave everything as it is (which currently means that I have several stock positions which are running quite well and a growing pile of cash which is just sitting idle).

I think that part of the problem is that it's a tedious process to get all my financial information from my various brokerage and bank accounts and then find the right metrics to see what to change to get back to my optimal allocation. Typically, I go to all the online systems, copy the balances to a spreadsheet, where I arrange them in sort of a balance sheet layout. I also track the information from my current account in a time series fashion to get an idea of my seasonally adjusted income/expenses (in particular, I separate non-stable outflows and compare them to the same month of previous years). Then I compute simple metrics like leverage and overall stock allocation. Overall, it's a cumbersome process and I don't feel I'm getting quite enough information out of it to justify the effort.

I thought that some of you guys might be in similar situations, but I couldn't find any threads on to how to analyse your own portfolio, so I thought I'd start a discussion (so this is not about WHERE to put your money but on HOW to keep track of it). How do you go about analysing your personal portfolio? Do you have software that you use, how do you arrange your data, what metrics do you look at? How do you include values which you can't get directly from a system (real estate)?