My concern is this: if I decided to do an MLO and made my payment directly to the Seller's lender, would I not still be in jeopardy because the other properties on the lien (which I have not control over) could default.

There are many posts here on biggerpockets about investors being concerned about the Chicago RLTO changes which state tenants can sue landlords for minor errors with the security deposit.

My concern is that I don’t want to be “low balled” or miss something on the deal, especially since this would be my first property.

I guess my biggest concern is that it sounds like you're creating three addresses right before selling. 

The price for electric is low during the spring/summer months, but i am nervous that this would cause high turnover should I choose to pursue renting this out even if i make this known.

You want a crappy enough truck you can actually use it.Then I have a nice sedan for DD duty that is comfortable, safe, and good fuel economy.Works out wonderfully, and its cheaper to have both than 1 nice truck.My issue is my Subaru wagon is really causing issues and costing a lot to keep running.

Not impossible but will take some effort.As far as property management is concerned.

As long as they didn't do something to cause the leak, I would say you are on the hook as well

Bedbugs hide everywhere and moving furniture can cause infestation to spread.

Even if I took a couple of days to inspect, I could still close that deal by Friday and then close again later that day to sell to my investor.It's not the "closing" part that causes the problems; it's the "finding a cash buyer willing to pay my price before my contract expires" step that trips up most wholesalers.