We also have a primary home with over $100k equity (5 years in possession) and are considering selling one or both to house hack a multi family and eliminate or significantly reduce mortgage.

There’s a lot of ways to make extra money that don’t require the traditional 9-5 job.

You may find a private lender willing to lend differently but if you want a traditional loan you may have to distribute more of the business income instead of leaving it in the S Corp.I would also make it clear that you own the business and only earn a salary for compliance purposes.

Is it a non-traditional lender. 

I can not go to traditional lending to get a loan.

I owe about $68k on it and believe it could sell for about $150k as is based on recent comps.Prop C: Single family, my primary residence in the Overbrook Farms neighborhood of West Philadelphia.

Liz - is the property  an investment property or is it a primary residence Do you need any funds  from this  equity now ….if not  - I wopuld recommend the HELOC  ...if property is an investment  property and if you want to ge the heloc in the LLCs name - you will likely find that there are not many lenders that  will be willing / able to  help with this  request

A traditional loan would be 80% of 500K or 400K. 

I feel that long term rentals using the BRRRR Strategy should be my primary method.

Our primary residence I bought before we were married and its in my name.