TLDR; What do I do with the $100,000 in my checking account?

I'm ashamed to even ask this...but I've been putting it off way to much and now I'm sitting on too much.

Age: 25

Occupation: self employed tech/programming

Objectives: Financial literacy and 20 year plan for income.

Risk Tolerance: Willing to take risks on technology. No fuel speculation

Current Holdings: No, $100,000 in checking account.

Assets: $2000 beater car, 42mpg. No home, properties etc.

Time: 5 year goal for apartment or home ownership. Build up assets over time so that when I reach my 40s I can live off investments. I live in Hawaii so it's rough.

Debt: No debts. No student loans. 2 credit cards with auto bill pay to try to build up credit.

Other: I live in Hawaii which is a super expensive city, similar to the Bay Area or NYC. My current rent is $450/mo, which is less than most condo's maintenance fees so if I were to invest into real estate, i would be spending so much more than my current. Cheapest places are in the $350k-400k range for 1 and 2 bedrooms. No family support/property etc.

Question:

I'm looking for were to best get started in investing $100,000 cash, diversified into 3-4 things, but without me having to spend months learning a new skill. I have a separate 6 months savings backup.

My own company pays me some income, but my main income is a $80,000/year salary with a matching retirement. If I put in 5% they put in 10%, so I plan to max that out.

What is the best place to get more information and what would you do with $100,000 cash right now? I'm psychologically afraid of entering the stock market now that it's showing "record highs" because I was told of a looming issues with the Feds possibly not renewing subsidies for the interest rate? I dunno.

What do I do?