@Vidit Maini Starting your business as an LLC taxed as a C corporation offers flexibility but involves double taxation unless you elect S corp status, allowing profits to pass through to your personal return.For tax savings, deduct startup costs, track business mileage or vehicle expenses, and consider a home office deduction.

I think it’s more about being flexible with your numbers.

From what I've heard, local banks are sometimes more flexible than the big guys.A buddy of mine managed to snag a HELOC on his rental property, which isn't always straightforward, but it opened doors for him.

The equity in my primary and other properties, combined with my income, provides the flexibility to borrow as needed—and I only pay interest on what I actually use.

In a soft insurance market, coverage is usually broader, lower deductibles are more accessible, underwriting is usually more flexible, and premiums are generally aggressive / lower. 

Does anyone know if there is any flexibility here, including if I can keep the HELOC if I have had it for 12 months (so stayed in the Primary Residence for a year after the HELOC started)?

It sounds like you’re setting up for a solid multifam portfolio—between you and your dad, the combined entitlements give you a lot of flexibility.

The buyers I resonated with, who I believed in as operators–those were the people I was willing to be flexible with.

If you can secure favorable terms now, the future development opportunities could offset any initial cash flow challenges.Communicate Flexibility: Approach the landlord with an open mind and emphasize that you’re willing to work with them to find a mutually beneficial solution.This isn’t a fantastical idea at all—it’s a creative opportunity that could work with the right approach.

You could increase the rent by a fixed amount to account for utilities, but a more flexible strategy might be to set a utility cap (e.g., $500/month) included in the rent and require tenants to pay for any overages.