Stock indices have withheld the test of time, that's where I've placed my savings as I wait to gather enough knowledge/cash to invest in a property. 

The souther area will have less (as the county tries to maintain a healthy housing stock for workers who might commute from just outside of Boulder proper into the city.)-- They also did away with one of the "types" of licenses.

, or my all time favorite, an amount equal to what they “would have made’ had they invested in Apple stock in 1986 instead of purchasing their home.

Goal: to have enough to retire by age 50 from cash flow from rentals, stocks/bonds portfolio.

High yield savings account, real estate debt fund or divide up the $100,000 between HYSA and index funds/stocks (with a higher percentage going towards HYSA if you want be more cautious). 

Dont suppose I'll get it...again, i've never done a real estate deal other than purchasing my house over a decade ago. without experience there's just so much i dont know.networking is a sore spot, i'm just not a people person. thats one reason i look at real estate. since i plan to have any properties managed, i wont have to deal with a lot of people. i imagine you'll scold me for this but whatever. i'm never going to be a people person and thats set in stone. it's something i have to work around not overcome.It seems I always get to the same point with real estate where I take the safe and easy route and leave my $ invested in the stock market. the thing that appeals to me about re, and i'm more focusing on rentals, non b&b, is steady income with an appreciating underlying asset. whereas the market is up and down. i can get totally safe 5% from short term bonds, but i know my principle is withering away from inflation (i dont believe the gubt bogus 3% cpi). with a rental house i could get 5% rental income, and the house will appreciate ~5% a year. that's a huge difference. the other thing i'm somewhat interested in is flips, but same story there, i just dont have the knowledge, and all the reading this forum or watching yt's in the world only gets to the surface as it's all airy generalities.

You were a 5% owner if you owned (or are considered to have owned) more than 5% of your employer's outstanding stock, outstanding voting stock, or capital or profits interest.If you file a joint return, don’t count your spouse's personal services to determine whether you met the preceding requirements.

How do debt funds perform when stock market go down? 

I have around 300k in a company stock account that does well with dividends, so don't really want to sell of shares.Would taking a personal loan or doing a margin loan make sense?

Or an alternate strategy if your goal is to have a vacation rental paid for is to buy some sort of investment, STR, buy and hold, stocks, bonds whatever and just dedicate the cashflow from that to renting a place each year.