@Steve VaughanOK, that's interesting, I managed to delete half my answer above.What I meant to say is that this would be such a useful trick to a DIYer because it means, on something like a simple gable roof like the one pictured, you could reshingle half the main roof in early September, tarp the ridge, wait out the winter, and then reshingle the other half in April.

If there are no places that are as cheap as that, then it is a good idea to live in the one half  while your tenant "subsidies" your living costs. 

I have a 4 bedroom a few miles away that I get $1,700 but this neighborhood is a little further out but it is walking distance to a very nice lake.  

For whatever its worth, I have been through the rough times and I would suggest you keep a portion o the equity line open and not used. like atleast half.

I was going to say two months rent but if it takes 73 days on average I'd go with option 3 and return the unused portion once the property is rented out (so if it takes 75 days return a half months rent).The good news is we're in April - a lot of people are looking for housing at the moment. 

It is less than a mile from I-94 in Elgin, IL.My question is what would be the best place to market this property on here?

My father wants to put up half the money and be involved.

I'm leaning toward demolition with intent to replace it with a structure about half that size but don't want to waste materials. 

I am currently looking at multifamily homes in my area with the intent to house hack for the next year and a half.

I will go ahead and clear half of it and then continue to clear the rest over the next few months.