The VA loan offers some advantageous benefits, and rates are predicted to continue to fall.

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? 

Not knocking Michael Blanks whatsoever bc that dude has it going on too.. but Tims operations and the way he structures every single deal he does seems a much safer, predictable route than majority of syndicators.

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. 

I'd also suggest running some for-rent ads, to see what type of response you get.It's notoriously difficult to accurately predict ARV on these types of properties, because they're so niche, and the market for them is usually completely different than the market for more standard properties...For instance, a lot of lenders won't provide a mortgage on a property for less than $100k--and if that's the case in your area, that would mean that the only potential buyers for the property are cash buyers, which makes selling the property more difficult.  

Its like the stock market.