My goal is to buy them with conventional financing, repair them to be rent ready (ideally less than 10K in repairs), and hire a property manager to rent them out.

Very quickly the major markets & players in those markets will become clear to you as we frequent these pages often.As for the concept of buying out of state remember that It's not really that complicated to buy out of state.

I cant remember the exact number, I think its 580 for the 3.5% down payment program. 

Remember, property won't be in exact same condition as it was at the time of move in.

I also realize this can possibly be claimed as a business expense, but this does seem like an exorbitant record keeping fee which could ideally be avoided altogether.Thanks guys,Cameron

I've wanted to be a mechanic for as long as I can remember.

Matthew, I feel  your frustration and remember being in  your shoes. 

Long term commercial debt lenders make adjustments but does not generally follow that.For high quality assets i am currently seeing about 4.8 percent for 10 year debt. 5 year fixed I am seeing about 4.5%.If a life insurance company they can go lower on rates but want minimum 35% down and more picky on the properties to lend on.Seller financing can be great BUT just remember to not way overpay for an asset just to get that.

I believe it's been done before but remember the cost to do so in some places can be very high. 

@Danny MallerNext time, and as you build your empire use the link below to look up any City of Chicago code violations. https://www.cityofchicago.org/city/en/depts/bldgs/...And if you cant remember this link just google "Chicago Building Violations".