@Kevin Hintz It's property dependent, obviously, but last year, I sold one a street back from the beach that they're cash flowing.

I'm going to exclude my personal residence from this because I don't view this as an investment, I need a place to live.Excluding my primary residence my current breakdown is 47% real estate 53% stocks/cash. 

Which one is more appealing - continuing to own the house or the security of that much cash/liquidity?

You'll have to look at the income and expenses to predict whether your cash flow will improve.

You will also need to front some of the cash to start the rehab before you get a draw approved with most lenders.

I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

When you learn to partner with professionals who are well-versed in this segment, most distressed property transactions are quite straightforward.Myth 5: Distressed Properties Are Not Obtainable with FinancingThere is this perception that distressed properties are cash-type deals.

Do I wait another year to save more, or do I look into a HELOC or a VA cash-out refinance? 

If it’s the only one, it might be worth negotiating rather than holding onto a property that will bleed cash every month.

And not to mention no stock matches the dividend rate one can get in real estate with such low risk/volatility. 20yrs ownership, oh-yeah, cash-flow on renting it would be HUGE now so it's easily comparable to a 20%+ monthly dividend, if not more.