When I explored this option in 2020 my lender said it wouldn't be possible because of occupancy issues (building was not fully occupied), and DSCR.

Am I required to issue a 1099 to my friend for his labor?

Been using it for a few years now with almost no issues.

Make sure to write down your policy incase you find yourself in a fair-housing issue.

The best cash flow is usually in D+ areas where the buy price to rent price looks great, but that comes with deferred maintenance and tenant issues a lot of the time.

There are some things that can cause issues with your upfront approval or end up causing a denial in or during underwriting that an unexperienced loan officer will not know or catch.One big thing to keep in mind is when you are buying more REI the guide lines require more assets and PITI reserves and a HELOC can "Never" act as an asset or PITI reserves.

There is no sense in ruining goodwill over a trivial issue.

I'd also be weary of any realtor who tells you it's not an issue.

Am I correct in my understanding that after the house is built and a CO is issued, we can work with a traditional bank/lender to get the new home appraised and take out a traditional mortgage on the home for XX amount (the amount owed to HELOC and hard money lender)? 

Managing multiple properties does come with its own set of challenges, like juggling different maintenance issues, taxes, and possibly even varying market conditions if they're not all in the same area.Here's where your financial goals come into play: Are you looking for a more hands-on investment with potentially higher cash flow from the get-go?