Section 8 is a tool for landlords, NOT a cure-all.Yes, a landlord can sometimes get higher rent via S8 than they can from cash paying tenant, but only in Class C- and D areas.

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."

Or does it purely my choice of whether I want cash flow or equity build? 

Bought for cash flow, got appreciation, and then exited with their winnings. 

Buyer's agent suggested "Cash to move out" but I'm not exactly sure how that matters if the tenant is HUD and needs a new HUD apt. 

I need to pull cash out. 

By the time we are our parents' age, our properties could be paid off/cash flow well, and we are sitting in an amazing position. 

The house is situated in a desirable neighborhood but it seems they are only looking into cash offers. 1.

So my question is, if you had the money to buy a property all cash, would you do it?

Most will tell you to replace all to cash the big check.