Using a heloc as 1st mortgage really only has a major benefit if you have idol cash sitting around from your paychecks. 

However, properties ranging from $100k to $50M or more have benefited from cost segregation.

But it’s clear you’re a smart investor who knows the long-term benefits real estate can bring.I keep reminding myself why I stick with real estate: you can make money every month in four different ways:Cash Flow – Passive income to live on.Appreciation – Long-term property value growth.Depreciation – Tax benefits that reduce your taxable income.Tenants Paying Down the Mortgage – Even if you’re paid off now, this is one of the biggest wealth-building tools for leveraged properties.It sounds like your main struggle is the stress of active management—and trust me, you’re not alone.

. - The ultimate house hack, live in the small ADU unit and rent out the two levels of the main house on AirBnb in San Francisco (I would have thought STRs are oversaturated in S.F. but it worked for them and they stay fully booked).

Not to mention the tax benefits it allows. 

Your property definitely has the potential to benefit from a cost segregation study.

If cash flow is the main goal, there are many other markets to consider before San Diego.

.- Depends on what you're doing specifically, but usually I'd recommend getting an EIN at least to give access to business bank accounts- Repeating #1, if you're going to a property and 100% of your time is spent doing renovations and the like, sure, but if any of it is for personal benefit, that'd be disallowed.

For the main house, I'd get a washer and drier. 

There are networking opportunities with the group after these meetings as well but it seemed like mainly people in the program and not experienced capital raisers that are there by design (but I could be wrong).