Biggest Mistake is putting all your effort into a deal where the borrower is not even fully on board or shopping mid-process.

A lot of borrowers shop blindly. 

And what questions should I be asking when I start shopping for a loan?

Have been looking into Commercial Retail shops, laundry mats, etc. but I am a bit unsure how much I could "purchase" with my current cashflow/down payment.

Similar with a SFH: I can at least get in the market with a 5% conventional loan not expecting cash flow but hoping appreciation will help me out in the next 2+ years and I will at least be able to put up the remainder of the expenses since I do live with my parents.I am young so I could be overthinking, but my end goal is to have a portfolio where I can cash flow enough within the next 5-15 years to let go of my job (5k clean a month).

Of course we all want the best of both worlds; that is a hidden gem on a secluded/private beach, but close enough to a town to find good eats, drinks, and shopping.

I live in North Myrtle Beach, have a large STR rental house in the Cherry Grove section of the beach, and frequent Myrtle Beach proper often for dining and shopping.  

In Denver, that's any of the numerous areas that has bars and restaurants and shops nearby.

So definitely shop around and don't just take one persons word for the full picture of what is out there for you. 

I do find myself shopping quotes frequently.