Hello @Abel Segura, and welcome to BP.There seems to be a plethora of members on this site with an anti Wholesaler mentality.

It is a different mentality and both are legit.

I always run my numbers on WCS (worst case scenario), but in today's market you leave SO MUCH on the table with that mentality. 

Deliberately have a few challenges in your screening process - it will weed out "entitlement mentality" problems4) Allow payment plans, but create system to track when payments due, so they don't keep falling further behind You will need to call them on due dates or they will fall further behind Be prepared to give a strong NO when asked if you will change rent due dates to "make it easier" for tenants to pay rent based upon their SSI or paycheck dates.

Given the market conditions and FOMO mentally from buyers now is not the best time to buy.

Even the mentality of not paying markup isn't valid.

However, once you look at enough properties and home inspections, you'll be able to quickly do the mental math on-site.

I feel like I'm reaching a mental block in scaling my rental portfolio.

I want to help him get out of this bizarre situation and the idea of "I can't" is really mentally straining to me.

Liberal Arts degrees and math don't go well together, so by math do you mean learning and mastering spread sheets, mental calculations, both, more?