@John Lasher If you are still looking to spend $20k-$30K for a coach, I would be happy to take you up on that offer :) For full disclosure,  I will share with you precisely what you can learn online/ perhaps even entirely through these BiggerPockets Forums but that doesn't address the reason why most are still unable to purchase larger assets: creditworthiness and capital relationships.

The successful wholesalers spend $10k + monthly on marketing3.

This allows the Board to spend the funds on anything, and if they do, the owners would need to restock the reserves!

Based on what my real estate agent thinks that this quote will be, roughly, and the after repair value, it looks like I could buy this property in cash, spend a month or two fixing the damage, and then put a mortgage for roughly 1.6x what I paid for it and thus have a cash flowing property at a few hundred dollars per month and a little more money in my bank account ready for a down payment on the next deal.

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

There are lenders out there spending a ton on advertising with an army of correspondent's funneling them loans and many can very well be one and done borrowers because the loan servicing/construction admin is lousy. 

I agree that is will be a gamble as to how well it will do.Also, ask the owner if they will entertain partial owner financing to keep from dragging family and friends into this risky business venture.Maybe even rent from owner for a year with right to sublease to see how it goes before committing to a purchase.

While I don't object to spending money to do one's due diligence, I don't know if $500 is called for when you can get very high quality syndication groups/meetups/information for free.

My ultimate goal is to become successful with my real estate investments so I don’t have to rely so much on my job and be able to spend more time at home with my soon to be wife and future children.

If it is a high-end project, I would spend on an actual lIcensed designer.