Obviously if you have unlimited cash then sure, don't do it but for 90% of people it is the cost of doing business. 

Combined this leads to high cost of leveraged purchases. 

I’ve been there, and I want to share insights that can save you from costly errors.During property tours, ask smart and relevant questions.

But the no up front cost option is great for basic updates and upgrades for a retail home seller.

Could be a low-cost loan or seed money equity stake rather than a gift to be more "fair". 

He’s also very rude and did not want to split escrow costs or even me a  real commission. 

Whereas I don't know if it will make up for the cost of software when only renting. 

If you are looking at this decision through the investment lens, what would you net on the investment that you put this money in to, after transaction costs and taxes? 

If you were not, you’d save the same taxes as strategy 2  Or 2) You’re going to spend money (capex) that will be added to your cost basis giving you a higher yearly depreciation.

Financially speaking, I'm still saving, but the goal is 50k saved up (all costs: closing, fees, down payment, portion of rehabbing costs) by this summer with my fathers help on the cash all while I continuously save 50-80% of my work checks to fund for rehabbing this property and I work off my second job and "survive off of that."