His company is Bullseye Real Estate We've used him mostly for small scale repairs, i.e. build a bathroom, repair the roofing, patch drywall, paint, kitchen install, masonry repair (front steps) etc.

In addition, owner loaned us $100,000 at 6% simple interest for one year to make major repairs (installed heat pumps, replaced boiler (for heating water only), replaced some siding and major roof repairs.)We were very clear with each other what we each wanted out of the deal.

You may pay 1.25X - 1.5X for a roof because you aren't repeat business whereas a GC uses the same roofer many times a year and they get a great discount.  

Even with holes/tarp on roof and plywood over windows, the place still smelled like smoke. 

The deal that pays all your costs may also come with tons of repairs or problems so its ok to buy a nicer property that will not need a new roof furnace well pump sceptic etc... in the next five years.

., testing main components, general mechanicals condition, basic roof condition, any major red flags, etc.) for a lower cost.

Can you imagine how much it costs to put a roof on that place?!    

Issues with the property at closing: low water pressure, aging roof, several lights not working, dated interior, water stain under HVAC unit, damaged decking (burn hole & rotting boards), old appliances, holes in drywallAnticipated cost to renovate:  $22500 (includes roof, repiping from old galvanized pipes, renovation of currently empty unit)  The currently occupied unit is TBD on cost, the tenant has been in place for the past 3 years.   

In my experience, relying solely on pictures can be outright misleading, they do not provide insights into the internal structures or the condition of the roof, plumbing, and wiring to say the least.

But you are talking the roof will get ripped off, etc.