Here’s my strategy and the issue:Current Strategy:Buy a property for $200k with cash.Refinance after 6 months to recover $150k, leaving $50k in the property.Use the recovered $150k to invest in another property, but I need to save up more money to repeat this process.Alternative with Hard Money:Use hard money to buy properties worth up to $800k.Refinance them later to recover my initial investment.For the hard money scenario, obviously I wont be buying them all at once, but rather buy a property worth 350 -> refi -> get HML -> repeat, until my money has ran out.However, hard money can’t be used for cash offers directly, as it’s typically a loan.

Yes, I hate seeing the suffering but I am a professional solution profiter, I make $ off solving problems so MORE problems is a giant blue light special. 

I do think new investors suffer from an overabundance of short-term thinking right now.Regarding number 2, I think your takeaway to buy smart is different than a result of wanting to buy more.

I suffered from shiny object syndrome also until one came up and slapped me in the face.

Its an LLC so I probably wont be able to make them pay for the roof repair, right?

If that's not the case and the GC still requires 1/3 payment up front,  it means they have other projects that are suffering or lack quality subcontract relationships and can't place them on net 30's and when contractors are moving money around to cover for other projects,  that's a slippery slope. 

I don’t want him to waste any more time and want to steer him in the right direction so he doesn’t have to suffer unnecessarily.

I find though many wholesale lenders wont let you do both in the same transaction.But for doing private money deals were its mandatory in Oregon to have the MLO

A person can lower there cost of ownership, help protect and defend the asset, help with maintaining it AND your not just some PM, you've got skin in it, you suffer if they suffer, you win when and only if they win, your interests are aligned. 

You are suffering from unsatisfaction and FOMO, but keeping your W2 is the best strategy for long-term wealth because you are lendable and earning the whole time.