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).  

I've seen this and it's the blind leading the blind.

Since it’s a new build, I was able to negotiate some great perks, like a 5.875% interest rate, no closing costs, a fridge, blinds, and even a backyard firepit.Pros:Good school districtLow interest rateMinimal CapEx and repairs (because it’s a new build)Low insuranceHigh-quality tenants (due to the school district and being a new build)Cons:Lots of new builds in the area, which could drive down prices and increase vacanciesThe Numbers:Price: $290KInterest Rate: 5.875%Down Payment: 25%Monthly Mortgage + Insurance + Taxes + HOA: $1,480 (I got really low insurance since it’s a new build and Alabama’s property taxes are low)Property Management: 10%Rent: $1,800 (this is under market because I wanted to rent it quickly—most units in the area were sitting vacant for 100+ days.

Please keep pushing and sharing your progress. we are enjoying seeing your success in addition to learning how to pursue and analyze deals in different market sectors before blindly buying and learning the hard way.

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. 

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.

Instead of spending years learning by trial and error, working with a coach or mentor can allow you to accelerate your learning curve, gain confidence, and achieve your goals faster.