Income:
$60,000 base salary + quarterly (~$1,000 but not guaranteed) and annual bonuses (~2,500)
Total: $62,500-$66,500
Monthly: ~$3,000 (base pay after 401k and taxes)
Current expenses:
Mortgage $1900 (property tax, insurance, principle, and interest included)
PG&E $50-70
Internet: $51
Water: $45 (bi-monthly)
Garbage: $50 (quarterly)
Food $250
Auto/Transportation: $62 ($40 gas, $22 insurance)
Public Transit: $180-$220 (bike to public transit 5 days a week, not possible to bike all the way)
Discretionary spending, bike repairs and other misc. expenses are usually <$100 per month
Worst Case Total: $2,708 (usually closer to $2,500)
Assets:
Cash: $31,100 ($20K+ in a CapitalOne360 savings account)
401k: $14,000 (current contribution is 20% + 3% match, fully vested in November, index funds through Vanguard)
Roth: $25,300 (max every year, index funds through Vanguard)
Rollover: $14,600 (leaving alone in an index fund, also Vanguard)
Taxable: $13,500 (index fund through Vanguard, auto transfer of $100 from savings account every two weeks)
ESOP: $17,500
Real Property: $375,000-$400,000 (current market value of a 3 bedroom, 1 bath in my neighborhood)
Car: KKB $3,000
Total: $494,000-$519,000
Liabilities:
Mortgage: $264,000
Current Savings Rate: 34% + additional that is swept over as my savings gets too big.
I currently live farther than I would like from work, I work in San Francisco and live in the East Bay. I bought my house with my ex-husband and the commute is killing, nearly 2 hours a day. Since housing prices have recovered for the most part I could get $375,000 on the low end for my house which would leave me with $111,000 in capital to invest (more index funds with Vanguard). If I moved to San Francisco I would get a smaller apartment for <$2,000 (rent would be split with my SO and reducing my utility bills). Anywhere within San Francisco I could ditch my car and the majority of my transportation costs by relying solely on my bike.
I am 29 years old, so ideally I would work another 5-10 years full time (allowing 5-10 years to transition into something I at least enjoy more than my current job while I continue to build a good cushion). Another goal is that I would like also like to be able to semi-retire and travel more in the future, possibly going to part time to accomplish this. Does this sound overly optimistic or even realistic?