1. Rebalancing is 100% a judgement call. Keep in mind that rebalancing every four years, every year, or whenever the market moves your portfolio away from your target allocation... all of these decisions fall under market timing. If you rebalance too soon, you are more exposed if the markets conginues trending in the same direction and if you don't do it soon enough you miss out on a potential reversal. For your Vanguard IRA (and potentially your 401K depending on your employer/provider) rebalancing Vanguard funds will not incur transactions costs. If your method works for you, stick with it... if you want to back-test other methods and try to time your rebalancing, do that. I would just understand what you are signing up for. 2. The idea of holding two portfolios also appears to be market timing. Add in the complexity of measuring your balance across the two portfolios and it sounds like a waste of time at best. Your diversified portfolio should appropriately expose you to the aggressive and less agressive strategies that you are talking about splitting into two different portfolios, no? I invest a small portfolio aggressively in indvidual securities outside of retirement accounts however I understand the greater risk of losing this money. I do not factor this money into my retirement allocation (although I might if it represented a larger piece of my portfolio, it is currently ~2%). In short, just be aware of the risks of any decisions. I admire that you reached out to get others' opinions and wish you the best of luck.

As a disclaimer, without knowing anything about the company I'm not trying to ascertain its potential. I choose to hold no employer stock but I can see the argument for holding up to 10% of your portfolio versus the 30% you apparently hold now ($200K salaries x1.3 = $260K non-company stock holdings). If there are required holding periods you could use more advanced strategies such as long term options to mitigate any downside risk of the companies' shares. In the end this is a personal decision. When it comes to the $2-6K in extra budget, I think you came to the wrong place if you're asking what to spend it on! I would use whatever is left after your vacation to build the larger emergency fund you mentioned. If the balance starts to get over the 12 months down the road, rental real estate could be an option and could offer some tax advantages (making many of your expenses deductions for your small business).

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I "waste" ~$150 a month on a gym membership for my fiancee and me. I use the gym nearly every day, network by playing squash, and have lost about 25 lbs since joining in January. To me it is an expense well worth it while I've gotten back to a healthy weight and made use of the gym's wide range of amenities (at no extra charge). However, I am only on a 6 month assignment and I don't plan on making the expense permanent when I move on. I think notably missing is HOUSING. Besides the obvious need, many people overspend on location and oversized accomodations. Because the expense is such a large portion of most budgets, even a small relative increase can outsize a daily coffee habit, etc.

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