So myself and my partners are currently in the market for what we planned to be our first single family buy and hold rental.  Our plan was to acquire 2 or 3 single family homes then make the leap to developing bigger commercial projects from raw land with a proven history in real estate investing.  Has anyone ever closed on vacant land or a property and demolished it to direct a larger commercial development project for their first deal?  I know I may sound ambitious, but I know everyone on this forum has to have big dreams and vision otherwise you wouldn't be interested in real estate investing at all.  Everyone wants the hotel in Monopoly not the four houses. 

Yes I have.

Yes, many times

You could sell the land raw to an end user, ground lease the land, entitle the land and sell for more money than raw land, or a build to suit for STNL.

Spec development is the riskiest because a lender generally requires so much pre-leasing before you have funds for construction.

You could also partner with a more experienced developer for a JV agreement and learn how they do it. You will usually not get much of the deal generally just a small slice as the larger JV partner is doing most of the work to entitle the land and develop it.

Definitely, but is it zoned for commercial? Do you have enough land for a commercial development? Have you checked the local ordinances on density, setbacks, parking requirements, etc.?

@Brian Lau

Doing a larger commercial project as your first deal out of the gate is ambitious. The advice that @Joel Owens is correct, partner up with a developer, and learn while watching them develop the project. 

Send me a DM and I would be happy to talk about it in detail. 

Thanks!!