A local glass company might be able to replace just the small, broken section between the leaded lines.

Tip: A Self Managed HOA that has no real estate experience and is managing the building = drama.Back to topic :)A healthy HOA should be able to tell you the status of the reserve account and whether or not the current monthly assessments consider projections for the next 10 years.

are there any investors who have made this business model work and can give me some insight on this to consider and tips on how to make it profitable and beneficial for these neighborhoods?

I have already learned some helpful tips that I plan to put to use. 

Anyways, and not to sound like a broken record, none of what I've written here is from personal experience but all from reading all those comments. 

Any tips on how best to broach this would be greatly appreciated.Thanks!

I'd guess 6-7 (my wife and I combined) hours per week on site maybe another hour or two on the phone per week.My tip is meet the neighbors and give them your number and ask them to call if anything is wrong.

I appreciate any feedback or tips you may have for a young student such as myself.

Scott's book on estimating rehab costs.These are just tips so you can make the best analysis of the deal and a solid presentation to potential partners. 

I am currently healing from a broken foot and getting around is nearly impossible.