I would only explore second-lien positions loans if your current interest rate is in the 3's.

Asking is $200K, my relative (buyer) looking to put 20% down.He is pre-approved for the amount, lender has prepared both a conventional loan and a mass housing loan option for first time buyers.Would be purchasing as an owner occupied "primary residence", rates are decent under both options.Condo is currently rented, tenant lease expires the end of August - roughly 4 months.Lender says both loan programs require buyer to occupy the unit within 60 days, to qualify for first time buyer deals.Is there a way to get them to extend this to 120 days (4 months) until the tenant lease is up?

With today's interest rate, this may be a viable option, compared to buying physical RE.

I typically advice a cash out refi over a HELOC if you have an immediate use for the funds since HELOCs have variable interest rates, but you also want to take your current interest rate into consideration.

I’ve had this itch to get into real estate for a long time, but everytime I start to dip my toes in I get the feeling that with prices/rates where there at it’s hard to justify pulling money from risk free 5.5% ?

That rate, TODAY is WAY low!!

The downside of the HELOC is the interest rate is usually higher so you will want to pay it off faster. 

Valuations prior to establishing residency is tax at different rate.

I would weigh those two options out and see what costs less overall between an entire new loan and or the blended rate of the two.

Nobody knows what is going to happen with rates...trying to guess or forecast is a fool's errand.