I paid for it with a LOC and am looking to refinance it into a loan.

If you ever wanted to refinance the property the loan would look totally different if you make it a legal 5 unit.

You can do this as a hard money refinance.

Ultimately a 1031 would have been the smartest move to buy another property and simply do a cash out refinance in 6 months to have access to some of the funds.

Wanting to scale quickly I've thought about doing a cash out refinance on the investment property after about a year and using that cash to pay off the HELOC then using the HELOC once again to get in the next property (rinse and repeat).

When it comes to refinance, you either will have to secure the appropriate zoning or obtain a special use permit to comply with local ordinances.

Try and refinance?

This can come at refinance, and the lender will want each portion to be appraised.  

With fees and points and so on, their money cost me 16%, and it was a total pain to refinance to a 5% conventional mortgage.If you are going to do a deal which involves buying a house for $50k less than market price, then paying Eastside $10k to expedite the closing is totally worth it.Eastside funding are good people, and they provide excellent service. 

Loans typically get paid back on a refinance or buy out period but if the property fails to gain enough equity within that period of time it can be a lost deal and painful.I would advise you to look into traditional or Non/QM financing where you use your credit score or income to buy the home.