However, my crystal ball is perpetually cloudy, so I try not to predict.

Cannot predict the future but I do see it slowing down (plateau) but not losing value just a slow progression.  

I moved here from upstate NY not long ago (I moved coast to coast a couple of times for school and work, but I plan to settle down this time).I've been investing in the stock market in the last few years, and always want to switch to real estate, but didn't know how until I found BP.

You can't control the weather or time the market precisely  (real estate or stock or any other).

Just a ballpark. 10K in savings, 120K in Stocks, 100K in 401kThe link below is the property I’m looking at trying to buy.

So based off this calculation I determined that my portfolio is strong enough to move on with my expansion plan into a new market.Business expenses as % of total expenses : 70% 1) Fixed Expenses: a)Monthly Mortgages: 45% b)Property Taxes: 18.7%c)Utilities Expenses: 14.8% d)Licenses & Insurance: 5.4% 2) Variable expense - Water bills + repair expense : 16%Personal Expense as % of total expenses: 30% My monthly living expensesa)Housing: 39.7%b)Child Care: 25.4%c)Living expense: 22.2%d) Food: 7.9 %e) Insurance: 4.8Income 1) Total Income - 100% A) Rental Income: 42% B) Wage income (W-2) : 26 % C) House Flipping Revenue: 23% D) Property Management Revenue: 5% E) Stocks/Dividends: 4% Please let me know if you would like help walking through this process as it has been super helpful to understand my financial situation or send you the spread sheet I used.

I have come to believe I should have a substantial portion of my net worth invested in a Schwab Total Stock Market Index Fund (SWTSX) or Vanguard Total Stock Market Index Fund (VTSAX).

Anything falling within that description would be self-dealing and result in severe tax penalties for the IRA.A self-directed IRA allows the IRA to diversify beyond the stock market into assets such as real estate and private lending, but everything is done through the IRA and exclusively for the benefit of the IRA. 

Though I agree with never trying to time a bubble or try to predict it and keeping your money on the sidelines is not the best move.

Sell and use the money for one, several, or none of the following:Put the gain in the stock market.Partner in a more passive way in real estate.