Real estate offers tangible assets that can appreciate and cash flow, but your IT business could also have growth potential, especially if you find the right help.Considering a Hybrid Approach:Since you’ve got strong systems in place for your online store and rentals, perhaps a hybrid approach might work—slowly transitioning more time into real estate while maintaining a steady presence in your IT business.

The neighbor Re-approaches the developer directly (neither realtor knows about the negotiations until later), and they reach an agreement for two of the lots.  

I like you goal but I think it would be best to build up as best as you can while maintaining a full time position.Thanks Ray, good advice and I know that's the wise approach.

I like the way you're approaching this!

You can creatively approach private money.

-Less repair costs, as elders are generally gentler on the home than families. 

Or another approach?

Having multiple layers of protection is a smart approach to mitigate the risk of not being paid back in a 2nd position loan.

I absolutely refuse to even speak with any of their guys when they approach me at REIAs and meetups etc.

If he was raising institutional money he would get destroyed by advisors if he took that approach.