My fervor and desire to jump into the game and become financially free was quickly deterred by people telling me I needed to get through school and start making money before I should get into REI.

I'm very conservative and want conservative leverage percentages, long-term fixed rate loans, high skin in the game and sponsor that has experienced at least one full real estate cycle and lost little to no investor money.

Spend some time obsessing and you can pretty quickly estimate how much money you can make if you manage the property properly. 

So, early on, right after college he decided to forgo the usual “management trainee” route and go right to where he could make a lot of money fast - commissioned sales.

My plan is to refinance the land with hard money, pay off my debt (40k) with the cash and then take over my rental property.

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It is foolish to continue adding late fees thinking you will make more money.

You don't have a full 12 months to fund the escrow account through your payments so the money is there to pay the bill when its due. 3.

So if you think the space is the best space available that fits your needs, in the grand scheme of business, you are not talking about a lot of money, so would sign the deal.  

I also don't believe that an asset should be costing you money every month.