First post.I own a plot of land in Boston that was considered "unbuildable" due to zoning constraints, but after a long appeals process I have a permit in hand for building a 3-family.

People with cash on hand ALWAYS get the best deals,  so having liquid money (in my opinion) is always the best way to go.

I don't know if that's a route I'd look into since my dad is already into real estate and intends to hand down the ~family business~ to me when I'm of age, I just need to know the ins and out of it all before I jump in, that's why I want to rent some properties of my own and perhaps do a flip or two before he passes the torch.

It isn't at all clear what you are asking, but I'll try to answer what may be your question.A handful of people are successful at real estate investing.

They may need a little hand holding if they've never done it. 

Don't take the law into your own hands.  

Have toured a handful of them and either the numbers don't work, bad foundation, located in the 100 yr flood plane and require flood insurance destroying cash flow etc etc. 

On the other hand, if you also have some interior demo to do, it may be cheaper to pay the higher "garbage is OK" price for the dumpster and just rent it once.I would plan on new flashing around the plumbing vents. 

Plus, I give them a $1,000 Option Fee to put some cash in their hand.- My payments (PITI + HOA) total $700/mo, but I rent the property for $1,200, so it has $500/mo in positive cashflow.

Ideally you want to be sitting at their kitchen table, contract in hand, when the truth dawns on them.