Estimated profit if I sell: 90-100kMy goal:  Buy an investment property and a primary property with a finished basement to house hack.   

HurdYou probably have some options, it seems depends on what type of property you are looking to refinance (primary or investment property),  what type of business net income or revenue your company shows, and/or business cash-flow. 

Does the way I buy the property make it easier or harder during the Refi process (buying as an investment property vs primary residence or second home) Thanks.

Our primary objective is cash flow, which is achievable there.

I was thinking the same.Without knowing all the details, and assuming you own your primary residence...I'd consider selling it (you'll pay no taxes on the gains) and then buy a house that you can hack. 

Kim,Congratulations, great way to get started by turning a primary residence into a rental!

@Steve Sonneson Regardless of the laws I've rented to friends and family in my primary residence and never reported it.

Also, I don’t have a primary home, so this is my first ever mortgage. 

Currently, I only have my primary residence, a single family home.

The primary 100k mortgage is now in first position the 25k HELOC is in second.