Index funds at current frothy levels doesn't seem wise.

@Jon Moore @Jake Walroth It is called the Court Index give the a call.

You know that disclaimer on your index fund propectus?

See map in the link below.https://www.epa.gov/sunsafety/uv-index-1#day1As for the windows...

Im wondering how much to invest in my Roth IRA and SIMPLE, HSA, vanguard index funds, and how much to leave in cash and set aside for buying a rental property.

Saw a REALLY interesting presentation earlier this week from an experienced investor- long and short it was based on a large pool of data starting spanning from the 1970's today and considered many metrics: employment, home equity, interest rates, volatility, foreclosure rate, affordability index, etc.... 

Then if you have left over money after that, I would look at investing it in index funds at vanguard (stocks/bonds) and learn the basics of that.Then after all that, I would spend another 6-12 months (you could start this now if you have time) researching and studying real estate.  

Public markets offer liquidity, but that comes at the expense of volatility and private investments offer investors low volatility, but with that comes illiquidity.The chart below illustrates how private real estate has minimal correlation to stocks, bonds and even public REITs, as measured by the National Council of Real Estate Investment Fiduciaries (NCREIF) property index (NPI), which looks at the returns of private institutional grade commercial properties.                              

At my 5 year mark, they sent me a keychain, a plastic plaque type thing the size of an index card, and a "gift" of my choosing, which I researched and found the highest value gift was worth about $10.

At a minimum you should be increasing your rent by a amount equal or greater than your annual cost of living index.