After 45 + years as a real estate investor, broker, lender, fund manager and syndicator, I’ve become aware that the “dream” of many investors and investor “hopefuls” is to be able to generate enough cash flow to live off their real estate holdings and accumulate enough wealth to make “work” optional.

Personally, If I could pull out a HELOC, I would use it to fix and flip which will typically make sense as you shouldnt be keeping the money out for that long and you can recycle it or pay it back and build off the capital that you got from. the flip.

Would love feedback from anyone with personal investing and/or property management experience in these cities.

Alternatively, your sibling might use a 1031 exchange to defer taxes by reinvesting in like-kind properties, though this doesn't directly fund a primary residence.Other ideas include leveraging a HELOC on the rental properties for the down payment, taking out a 401(k) loan, structuring an owner-financed agreement, or a lease-to-own arrangement.

I would spend money to enhance and update to current standards the search functionality and person to person tagging so it's easier to find stuff.

I'm really busy with my w2 job working all the time to fund my investments. 

Your ability to connect with them on a personal level matters more than your offer.Think about it:  • The “Used Car Salesman” is only focused on closing the deal as fast as possible.

If a person has RCV or ACV policy makes a huge difference, than question of what coverage level people had and if they had policy add-on's that cover cost over-runs and all that fun stuff, not to mention contents. 

I also personally feel like I may take a step back from my main biz in about 15yrs..

Perhaps there is a relevant book or podcast that you could suggest to expand my knowledge in this area.Considering you're experience with creative finance deals, which you mentioned previously, I am keen to hear about your personal insights and experiences.