If a citation happens then you have to deal with the courts, (TIME & MONEY) spent on having your project held up and last, having to get the project designed, permitted and possible managed by a general contractor "depending on the structure".Just be aware of your city, state & county codes before undertaking tasks that can be very costly.

( meaning this in the long term commitment that you are undertaking needs to be more than money buds ).4.

That is quite the undertaking, but smart if you send out that much mail. 

You should delve into the financials of the HOA if you undertake this.

This is a risky undertaking.

@Thomas Lee Nuckles @Elvin Tolentino Here is a graphical representation to your dilemma to help you in the quest for answers:

What seems like a massive undertaking while going through it, it will always seem less monumental looking at it in the rearview mirror.

It can be a big undertaking, although there can be profit in it IF the numbers are right and IF you have done your homework to know what you are getting into (both big “IFs”).

Time compared to a lipstick remodel much longer.. permitting process's etc.So for the one to two a year person I would think remodel is more appealing.for us we have morphed out of remodel into new construction.. and specifically either high end infill in happening cities like ( Charleston SC at 550 to 2 million per home) or move up track homes in Portland Oregon at 430 to 500k per and in those cases we have been buying 20 to 30 lot little housing tracks so the efficiency when you move up is we can build out like we are doing now  23 homes once we start going vertical we will build and sell them all in 12 months done money in the bank.. to try and source 23 rehabs in Portland would be a major undertaking and then trying to get the labor to work on them and finish them also tough to almost impossible..in todays market.. 

Many Associations or Condo's do not permit individual owners to undertake these efforts themselves and instead retain counsel on behalf of the building/subdivision at large to fight these ever increasing liabilities.If and when you decide to invest in Illinois, I would suggest reaching out to a local lawyer who handles these matters to determine if relief is possible.