When you are buying property, how much property you are talking abut really does matter. If you want to buy a house to live in, they care about your income, your personal ability to pay the mortgage. If you are buying a 20 unit apartment building they care about the occupancy rates and your ability to keep it occupied. It really as simple as that. The deal factors change with the size of the deal. But within certain ranges, the factors don't change at all. Buy a 10 million dollar house to live in, they still care about your income. Buy a 1000 unit apartment block and they still only care about occupancy rates and your management experience.
Now, I've estimated, planned, negotiated and sold dozens of technology deals that exceeded 3 million. I've done the same for a double handful of 10+ million dollar deals. And I've worked on one or two that reached the 50 million mark. The thing they have in common is that when it comes to the estimates, the plans, and the negotiations, the factors don't change. The delivery changes drastically, the oversight and number of hands in the pie sure change, but the actual work involved doesn't. The steps you go through, questions you ask, information you need to digest is basically the same regardless of the size of the deal. Which you only realize if you've successfully done it a few times.
Just like my friends who are think buying a 5-unit townhouse is the same as financing their second mortgage. You can always tell who has come out the other side having learned something by the way they approach their next deal. The ones who only survived their deal, who came out the other side but weren't changed, haven't evolved, who didn't learn anything, they're the ones who approach every deal the same way. They have a hammer that works, and they just keep whacking away assuming they'll hit some nails eventually.
If you want to make sure you aren't one of the un-evolved ones, make sure you are seeking first to understand. That's a little phrase I picked up from someone much smarter than myself, but I find myself using it way to often. In my mind, it sums up the attitude of the nimble among us. It separates those who are continually learning, from those who think they've got it figured out and are waiting for the world to agree with them. When you play in the realm of architects and executives, you see both attitudes often enough. Most of being a great architect or executive is being willing to make decisions, to hold a vision in your head and be articulate about that vision. This means there is a very fine line to walk when you are surrounded by ambiguity and collaborating with numerous conflicting opinions and personalities. You have to be very nimble or you'll quickly end up on the wrong side of the line.
If you are seeking first to understand, you will spend more of your time upfront listening and questioning. But you can't spend all your time there. At some point you have to discern the relevant information, express some decisions, be willing to wrong and allow others to correct you, and then drive for consensus. You must engage first to understand, but if all you do is understand and can't utilize that information, the value vanishes. You can be told the difference between financing your home and a multi-unit dwelling, but if you don't chance your approach and act on the information, you've lost the value. You are just as effective as if you kept hammering away with your single tool.
When it comes down to it, it is the size of your ears that matter most. But a nimble attitude and brains are also needed if you don't want to look goofy.