This will help you get through the frustrating times that you will definitely experience executing this strategy.

I have a decent amount of savings but can't afford to just blow $4,500 with no return.

You have to be very, very careful with personal possessions in Chicago as the land lord tenant ordinance can be frustratingly tenant friendly.

They couldn't manage the properties (collect rent and afford the repairs) and fell behind on the mortgages and filed bankruptcy.

Yes I plan on managing myself until I get enough properties that I can afford to pay a management co. 

@Pete BarrowThe market we live in (Chilliwack) used to be affordable, as of the last 2-3 yrs things have really taken off and purchasing any rental properties in our area simply do not make sense, that is unless you are putting down a very large down payment to bring mortgage costs down... but we have recently noticed things have started to cool off and pricing is taking a bit of a correction.

I just wanted to make sure what’s the plan it you don’t have a tenant and you can’t afford your hard money loan monthly payment.

This is called affordable housing or variant of... and it's used by developers mostly to either get approval for things or tax breaks.

Then follow through with whatever option the tenant chooses.It is especially important to rent it out before winter so if they can’t afford it anymore this is the time to move.

You'll get a much better result and will save yourself a lot of frustration and angst.Best of luck!