BP Experts - I have a friend who has recently told me he has an IRA that is not invested well and would prefer to invest it with me. 

I have friends in the area who are renting out bedrooms for $400 per month in an apartment so it seems like just another way to improve the cash flow of the property. 

Any family/friends that trust you and will give a reasonable loan to help with a down payment?

I'd start locally by asking friends and family for a trusted contractor they've worked with. 

I have an architect friend that has been working on similar projects in the Bay Area and Truckee.

The tenant says they have a friend interested in apartment and that this friend would pay this previous occupant their deposit.

If average cap rates in an area are 6% for a Class A building then you may be able to put value closer to 6.5% even 7% depending on the local market (I would try to make some local broker friends) if it is a Class C.

Can anyone refer an investor friendly real estate agent for Chicago suburban Lake County? 

But I know that full time agents often do all sorts of wonky / crazy / unusual / ill-advised stuff that has the potential to screw up the transaction when they personally buy/sell, or are representing close friends or family, so that might have something to do with it.

I’ve been talking to a close friend of mine about getting into fix and flips homes.