Syndication means I have to find syndicators, split the pot and more importantly align on goals, desires etc. 

Yeah, that makes sense to keep the pot churning.

Each room I charged the same rent rate for and rent covered all utilities.Kitchen: Fridge space was a little bit of a challenge, but it was more-so cleaning it out... we pooled food (split the bill) but all of us were the same eating style and one of our roommates directly benefited from us cooking his meals.

Move on to the next option or sit and bemoan the fact that someone won't hand over a pile of cash to someone who doesn't want eat their own proverbial cooking, up to you.  

You guessed it: the financing.I'm pursuing buy-and-hold, SFH.I don't have much of my own $$ to throw into the pot, so here's what I'm thinking:- Figure out about what a house would cost (I'm told to expect ~$200K - $250k)- Assume a traditional loan, and needing 25% down- So I'll need to raise ~$62,000 for the down payment- I approach friends and family, network with potential investors to raise those funds- Bank supplies the loan for the remaining ~$180,000Something like that.Should I speak with a real estate attorney before approaching those potential investors?

Don't allow cats.No matter how much you spend to 'smell proof' your unit there will always have some kind of stink either from their cooking style or their pets when they move out.

My in-laws also want to help offset cost of college tuition but i don't think the in-laws money and the business account money should be counted against or show a larger pot of money available for college tuition. 

Illinois ranks as the 2nd-highest effective tax rate in the country at 2.03% (although this could be skewed by the tax rates in Cook and Will Counties). 

I wouldn't bother changing the color ($$) for a rental if the siding is still in good shape.I'd also get a couple of big patio pots & put colorful mums in them (it's that time of year already) & put one on either side of the front door.

The tax and regulatory environment in Cook County is dismal.