Please try not to confuse two totally different aspects of investing when giving advice.

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 don’t want to spend a month in a dump.  

There are several aspects of a long term lease that are not needed, or additions that should be included in a mid term.

Plus I recently got a brand new calculator, wanted to see what out of state investors though the most important aspects of deciding between to similar rates cap rates in 2 varied size apartment. 

This is 100% the most misunderstood aspect of rental income. 

As I am new to this and looking for cashflow using rentals, one key aspect of this investment is to ensure that the unit rents out quickly and while I do understand that cash flow to begin with might not be attractive, it can be a good investment in the long run if the location is right(as appreciation also kicks in).

I 100% agree with the intent aspect and that is an important premise, but the fact is in this particular situation intent for it to be personal use has been confirmed (by way of a public post).

You can spend your time in worse ways, like watching some silly movie.