The truth is, a good host will spend time managing each rental.

I know it is expected that you will need to spend some money after someone moves out but I just didn't expect I was going to need to spend appx. $10k to get it rental-ready. 

The entire focus is on new people because they spend on more.4.

That’s a necessary tool that has some different aspects to it that allows you to see the WHOLE picture.

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).

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 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).

Outside of real estate, I enjoy spending time with family.  

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.

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