My total of all annual expenses is about $220K- everything, insurance, haircuts, leisure travel, property taxes, etc all included in thereI dont want to semi-retire any time soon, but I think it's smart to have long term plans.

I believe in the beginning I will get a lower return doing this myself, however education is always paid for somehow, right? 

Looks like it is actually better for the owner as well since if the property management company gets sued and they don't have liability protection, they might charge the owner for the expenses. 

You should also thinkgholding costs, the longer you rehab, the more expensive it is because you won't have a tenant paying rent. 

Drive a 2009 car that is paid off.I'm taking this next year to rent in Chicago (rent is about 1600/month) but am starting to seriously think about house-hacking and want to start talking numbers now so that I might be ready to close about a year or so from now. 

It currently rents out at about a $100 cash flow including expenses. 

Some lenders will offer you 100% financing but it will be expensive money to borrow. 

It has been performing very smoothly, zero unexpected expenses + having the rent steadily in my account every month.

yes, i did, so far i am able to get the quote from AAA (of course it's very expensive :) )

For example, if I need a tub surround replaced, they get paid $125 (I supply all materials, so it's strictly labor).