Walk the property as a Buyer.Without having physically walked through it, I can only provide limited feedback, but here were some of my observations.....The front brick looks tired, and there appears to be some patchwork..??. 

Benjamin, no peeling of paint was observed.

Just an observation.

There are two ways for you to get the actual then....1) if no one is willing to bid that minimum bid (what you are already out of pocket for), then you get the deed. 2) outbid everyone else if the bid opens beyond the minimum.An observation......the bidding at these auctions is competitive, and prices approach retail, if you get the property for what you're already into it for because no one was willing to bid higher, you did Not get a good deal.  

Repairing the roof first allows you to observe if the foundation water issues have been resolved.Make the property secure, waterproof, airtight and foundationaly solid first.

The quality of the Lincoln District does indeed vary dramatically street by street, and I would encourage you to drive around during both day and night to observe.

Note.. due to the circumstance that indeed good roofers do not want to do anything unless you change entire roof... but frankly speaking this is overkill..In fact i observed similar overkill in other professions.. in electrical, hvac you name it...... all through the back of my warm sit...simply by watching tons of youtube videos and courses...The real danger in investing into commercial real estate or any other real estate is not knowing inner details of the trades.........   

You are asking the right first questions and your observations about how many ways there are to make money in REI is spot on.

@Max Denning.If you're self managing your own machines than it's a guessing game, and you'll just need to be observant in order to develop an effective schedule.

Go and observe first.