I will give you a few pointers on how to spot good siding for the future;The seams are staggered, meaning they do not line up, which is good because you don’t want it to look like a vertical line.The seams are “topped” in the same direction.

The property is in a prime spot to build duplexes or single family homes.

I asked myself many questions in the beginning when I spotted a prospective property.

It will be really squeaky and tight on money, but maybe Dad could spot you some 'gift' money that if disclosed, should get this bird up and flying.Or, IF (this is a BIG IF) you are confident that you could make the payments no matter what on the existing HELOC, you might talk to Dad about putting the property into a proper Trust, and take the property subject to the existing loan via a transfer of the beneficial interests of the trust.   

Hey John, you're searching for that sweet spot, pretty much what I'd say a majority of investors here are looking for also (including myself), so you aren't "wrong" in your criteria... you're just competing with everyone else for that deal.

The second one is renting $200-$300 below market at $1200/mo since the owner is a retired 77 year old living remotely and just wanting a low maintenance property, and the property manager is the owner's old friend who primarily wants a reliable tenant who pays on time (she's been getting several subpar applicants).The unit is in a great spot less than a block away from the metra train that goes into downtown Chicago, and in the center of all the stores and restaurants in the little town.

There are 2 parking spots in front of garage door, and 2 on side of house.

Not that you're focused on appreciation, but I'm sure you'll see some over your hold period.Also, the neighborhood between Toepperwein Rd and Live Oak's Main City Park seems to be a good spot to look. 

One of my rentals has a ductless heat pump and as long as it is placed in the right spot, it works well. 

PBS Realty just handed me the keys on the spot!