@Mitch Holmes With $400K-$500K in cash and your contracting experience, start with smaller flips in the $300K-$400K range to minimize risk and build experience.

With the new rent control policies, there is zero incentive to lower rent as it may take years before you could recoup that with the minimal increases they allow. 

Also, having to interrupt stays to replace later doesn't make sense. 

They understand that there's value in what they provide, which is steady, documented income, minimal turnover, steady payment, quality references, no drama, and peace of mind.

Also, I’m not into tax evasion necessarily but she’s owned the place forever and has minimal taxes.

Investing as an LP in syndications/funds can be a great way to gain real estate exposure with minimal time commitment.It's key to invest with the right sponsor that has track record of delivering returns (ideally been through at least one downturn).

For minimizing upfront costs, FHA is better; for liability protection, conventional with an LLC is ideal.

Despite its high purchase price, the neighborhood's strong market demand and low renovation needs made it a promising investment for maximizing profit with minimal turnaround time.

In other words, I want to make the argument that even the worst-case scenario is better than allowing the house to sit vacant for several years while meanwhile paying out-of-pocket for taxes, minimal heat, lawn care, etc.

I'd minimize the risk of having negative cash flow in the first 12 months when things are the most unknown and I'd be able to increase the gross rent of the property which should give me a better loan or at least bigger margins to cover my risk for negative cash flow.