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.

However, we want to refinance right away, pay off the LOC + repairs, and take some cash out to purchase more properties (BRRRR method). 

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

I know the area well and condos haven’t done much of anything in regards to appreciation in the last 2 years, so I’d be concerned nearly all of your down payment will be gobbled up by commissions and closing costs if you sell, unless you got a downright phenomenal deal on the place or made significant improvements.

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

The good thing about the fees is that they cover some of the expenses lawn and plowing, much of the insurance, trash, sometimes water/sewer.The big thing is to read the association bylaws concerning rentals, often they require owner occupancy for one year, or they a have limited number of rental units.

As long as you know the rules about tax sale investing so you avoid the ways you can get hurt, this is a high return, low risk method of investing.

BRRR are impossible to get under a VA but using the method above it is possible and paying 6 months worth of PMI in order to make deal seems worth it to me.