I will be fully transparent that I always have a healthy dose of skepticism for anyone that is selling courses.There is certainly a value to being spoon-fed information.  

Each person has different goals, expectations, lifestyles, resources, etc. so we really need to look at the overall picture to see if this makes sense compared to other options available. 

In a healthy Association, they've taken into account that this will need to be replaced, and have planned for it, essentially charging everyone who has lived there over the last 20 years a nominal amount to be put toward the new roof when it's needed.With an unhealthy Association, they try to keep HOA dues artificially low, and when a repair is needed, they levy a Special Assessment, which puts the financial responsibility on those who live there currently. 

But statistically, how many actually CHANGE their lifestyle so that they actually pay off those Credit Card/s?

After considering a number of places I decided Wisconsin was best for my lifestyle.

The lender is now the barrier of entry of their risk appetite and they'll need you to gauge if it's healthy or not-- it's not your job, but there's too many headwinds for them not to do that.

It looks like you have a healthy spread from purchase to ARV. 

Therefore, money for renovations was handled before I provided a healthy budget. 

The time, energy, and lifestyle capital can drain your resources when you need to visit, build your team, manage your team, and how and when to exit. 

Granted, it's Ohio and not seeing appreciation like we've seen in Florida - but this area in particular is seemingly healthy.