Thanks to everyone that contributes to this forum. Especially those of you that have contributed to the wikis. I’ve been pouring over the site and the boggleheads’ guide to investing book the last few weeks to try and sort out my portfolio. I’ve got a lot to learn.
I’ve been very fortunate in the last few years on two fronts. My company granted, for me, an unusually high number of RSUs a few years back and the company has also went through a rapid growth period (stock has risen over 350% in 5 years). I’ve been somewhat remiss in selling off the RSUs and just holding it in cash with no real plan. Figuring out the kid’s 529 recently has finally forced me to get my act together and start addressing the situation.
EF / contingency: 100k
Other cash: 250k
Debt:
house - 680k @ 4.5% Mkt Value ~2M
rental unit - 350k @ 4.125% Mkt Value ~1M 3.5k rent
no cards or loans debt
Tax: married filing jointly
tax rate: Fed 35%, 9.3% State
State: CA
Age: 37, spouse 41
1 3 year old kid
Desired AA: 80 / 20
Desired international allocation: 30%
Current retirement assets (% don’t include cash on the sidelines)
Current AA: 93 / 7
Taxable
66k (11%) VFIAX Vanguard 500 Index Fund Admiral
185k (30%) company stock
401k
350k (57%) Vanguard Target Retirement 2045 (90/10 AA)
HSA
10k cash (1.5%)
Spouse
30% employer’s stock
70% various mutual funds in 401k
60k cash
529
50k vanguard aggressive age based (just opened. treating as separate from retirement)
The priority at the moment is sorting out my half of our portfolio. Obviously my spouse also needs to diversify the company stock; sorting out my half is leading by example

Both of us max out our 401ks every year. Going forward I plan to contribute an additional 12 - 20k each year to the taxable investments.
My spouse will be contributing $400 a month towards the 529 (I opened it with a one off lump).
We would like to continue working until we are 65.
We like to keep one year’s of expenses, including the ability to carry the rental unit, in the event of a downturn / layoff (our area is HCOL and tends to go through boom and bust cycles). This money is sitting in a 1.25% ally savings account. I will be moving half of it into ally’s 2% 1 year CD later today / tomorrow (thanks to threads here bringing it to my attention).
Outside of the EF / contingency fund I have another 250k in cash. I estimate I will have an addition $120k after taxes from selling the remaining company stock. I plan to invest $170k of this as one off lump.
The other 200k is in a holding pattern. It has been a bit of a dream fund for either moving across town or putting a down payment on an additional rental unit. House prices have almost doubled in the last 5 years in our area so we are starting to re-evaluate this fund. It may just be invested into the general portfolio sometime in the next 6-9 months. Toying with this idea, and re-reading the wiki on AA many times, are the main drivers that are shifting me to an 80/20 AA. The other option, of course, is to toss it into the existing mortgage.
Current Plan
I am planning on moving to the 3 fund portfolio and bringing my AA to 80 / 20 (excluding the contingency and dream fund). I am thinking of the following:
Taxable
11% - VFIAX Vanguard 500 Index Admiral
29% - VTSAX Vanguard Total Stock Admiral
401K
10% - VTSAX Vanguard Total Stock Admiral
30% - VTIAX Vanguard Total International stock Admiral
18.5% - VBTLX Vanguard Total Bond Admiral
HSA
1.5% - TBD
If the market “crashed” I would switch VFIAX over to VTSAX as part of loss harvesting
The California HSA is a difficult one given it's a taxable account from the state's pov. The idea of ~10% of all new contributions, between the two of us, going towards TIPS seems excessive. I go back forth on just sucking this up and doing the double ledger thing for feds and CA versus just investing the 6k in a taxable account. I need to re-read the various HSA threads and play with turbo-tax to finalize my decision.
Questions / Concerns
1. If we end up just plowing the “dream fund” into the portfolio then my 401k is less than my taxable investments. For re-balancing purposes, should I consider having both total-stock & total-intl in the 401K and taxable accounts so I can re-balance within the 401k entirely?
2. For rebalancing between domestic and international stocks I assume, unless it’s a gross imbalance, it’s best to just divert new contributions accordingly if both are not in a tax deferred account.
3. My company offers both a 401k and a Roth 401k. Am I correct in thinking it's something of a toss-up given we are currently in a high tax bracket?
4. Am I correct in thinking that it’s a toss-up between holding total-intl vs total-stock in taxable?
5. Is there anything obvious that I am missing?
Thanks in advance