Are their structural or hidden problems with the property he/she has not disclosed?

Here is a blog where I wrote about a recent 42 unit we bought and did creative things to add value. https://www.biggerpockets.com/renewsblog/bought-multi-million-dollar-apartment-complex-age-26/Just a few ways to produce ancillary income:- Laundry Coin laundryDetergent/laundry essentials in a vending machine in the common area laundry rooms.Rent individual W/D to each unit-Parking Garage parkingCovered parkingprime spot parkingJust plain old charge for parking-Renovations Interior units upgradesCommon area renovationExterior upgrades for curb appeal-Vending machines In common areas such as exercise room, pool house, laundry or leasing office-Trash pick up service In high-end buildings they have a service where you can set trash outside your door and for a fee maintenance will go around each night and collect it so the resident doesn't have to carry it to the dumpster.

I do not want to assess any late fees, yet at the same time do not want this to become an issue going forward.

Though some are adding a rental registry with a fee, usually justified as an inspection cost. 

With what the owner wants to walk away with/owes in taxes/my assignment fee, the price is still 60 cents on the dollar, but you are buying the squatter. 

Lesson learned...we purchased a SimpliSafe home security system that we can now move from project to project and has only $15 a month in monitoring fees.  

Unless your profit is really good I would make sure the investor purchasing the home understands they will need to pay their agents fees.

Getting a loan from family or friends is out of the picture, i found a local credit union that is willing to let me apply for a home equity loan but that is not guaranteed  and there is also a $300 fee .

With all the fees paid and taxes levied on cashing out my IRA, could any of that "loss" offset my capital gain on the sale of my property?

I'd be happy to discuss our fee structure with you and see if we're a good fit for your needs.