(Roof, box gutter repair, outdoor concrete stairs/walkway replacement, HVAC replacement). 

For example, a normal residential loan would expect  a roof, functioning utilities, etc. 

Less risky, because it's still a roof over your head and you can see what performs the best.Good luck with everything!

the challenges with flips  is that there are so many angles to try and cover / consider that it is somewhat like spokes on a wheel… even if you just take it system by system… roof, plumbing, AC, foundation, subfloors, electrical, appliances, septic, materials expenses, holding costs, taxes, etc.  

The major factors like the roof, furnace, plumbing, electrical upgrades, and foundation repairs are all examples of costly expenses you'll want to inspect before closing the deal.

Additionally, if their capex budget was only forecast for 5 yr hold, and they are now anticipating 10 yrs, they may be seeing roofs, exterior repaints, other exterior repairs (stairways, railings, parking lots) that they assumed they wouldn't need to address, but now need to.Things to look for: positive DSCR TODAY, not on pro forma numbers.  

Some common items to note: roof, electrical and plumbing, window updates.

For this reason, it wouldnt make sense to rack up all the fees for title, escrow, lender fees, etc to do an investment cashout when you likely could get a personal loan at a similar interest rate, but only pay 300-500$ in document fees vice paying the 5-8K fees you'd likely rack up between the lender and title company with the refi. 

So the house wound up needing the drywall, kitchen, bathroom, roof to the garage, Plumbing, Gas and other stuff done. 

Costs the same to put on a new roof.