The property is worth about $280k and I owe $178k.So my question for you is would you:A) Cash out refinance the property, shed the PMI, but have a higher interest rate-Or-B) Pull a HELOC out on the property and use that cash to fund another property, leaving the interest rate where it is on the mortgage, but also leaving the PMI on the property?

My recommendation would be to invest in some kind of index mutual fund and contribute maximum for the next few years, then you'll have a lot more investment options to consider. 

I currently have the funds to do this myselfHowever a family member wants to get in on investing as well.

But most of the people who were being foreclosed on were home owners not investors.So to protect yourself, make sure that you can cover payments when vacancy goes up and make sure you are cash flowing enough to cover expenses still if the rental prices dip a little and save some of the cash flow for an emergency fund - maybe 5k per unit. 

You are not a creditor who is seeking a portion of the funds.

Hard money typically has points minimums and you would end up saying 5-10% in just points to get funds for the remodel.

@Shu Zhu if you are comfortable lending the funds to your customer then go for it. 

I know I could contact a Canadian Bank, but would rather look for private funding as opposed to a conventional mortgage loan. 

Less than that I would probably just sink money into my vanguard funds. 

Separation can sometimes simplify borrowing money, depending on the type of funding you're using. 6.