I did a quick search under Chicago's real estate board, and there are a ton of entry level jobs you can apply for.http://chicago.craigslist.org/search/rej?

It'd be much easier to sell or develop the land if everyone is on board. 

Well it appears that most of us did OK for Apr rent based on the replies from many on this board, but now with May coming around now, let's see how we do as a group. 

There is so much confusion on these boards regarding metrics- cap rates are only for commercial properties, five units or more.

I would also recommend that you educate yourself on what it takes to get investors on board.

Since then we have done one BRRRR a year and my husband is totally on board now!

I'll definitely go back to the drawing board with the inclusion of the acquisition fee and simulation the various split scenarios you described. 

Financial decision regarding repairs or HOA fees are decided by a board and you will subject to their decision.

One board member is concerned that doing this would change our HOA from being non-profit to a for profit business and would require us to become ADA compliant (historic building that does not have elevators), pay extra in taxes, higher liability, etc.

Then after the Zoning department Denies it, your Architect needs to apply for the Variation/Change, you need to hire a Zoning Attorney to represent you for your case with the Zoning Board of Appeals and you get put on the schedule for the next meeting which only meets once a month.