I can see this becoming a major problem in the future so I wanted to have a plan of action.

Properties that grow significantly in value provide the equity and leverage needed for future investments, which can multiply your returns over time.

Having a vision for future projects like the ones you mentioned are great, but learning the ABCs of RE with a small investment (initial down payment - since you only need 3.5%-5% down on a primary) is the best way to sharpen your skills.

Thanks for sharing, the POA to access the original docs is a great idea, and I'm totally stealing it for the future. 

We sold a house with a low rate that would have cash-flowed really well because I saw the future deferred maintenance.

At this point, I'm not willing to sink the funds for a paid CRM service but may be open to it in the future.

This way I get paid upfront for my work 1-2k plus I know I have another payday at some point in the future if the deal closes.The costs to fully develop a property and sell for near retail usually involves the costs below and takes 2-6 months or more in some cases, but the profits can be huge if you're working in markets where land costs are high:Title 200-400Legal 500-2000 depending on zoning issuesIf wetlands are present AND its a buffer zone project: 2000-5000Perc & septic design if needed 1500-3000Treescaping & cleanup for retail sale 500-1500Selling costs of 6%I tend to stay clear of properties that need more than the above expense items.  

Explain how difficult it will be for them to rent in the future.

Instead of liquidating 1k in the stock, can I just give (transfer) him 1k in stock if he is OK with that (assume he is good with the investment and potential cap gains in the future)?

You know how to get a hold of me in the future and I'm always happy to help however I can.