I recently spent $5200 in roof and AC repair on the same house in the same month.  

He also offers investor inspections which don't come with the detailed report on every little thing wrong just the big items structural, mechanicals and roof.

Its a good learning start for you and even if you pass it up you will know so much more for the next one,   Its an old house so you need information on what they have done with the electric plumbing heat/ roof etc.You are on the right track.  

I found 2 that showed major signs of roof damage.

This is our first time doing an FHA 203K we are not doing any updates to the kitchen nor the bathroom just making sure the house is functioning running new electrical wire, repairing plumbing, back stairs, doors, few windows, painting, roofs, garage doors, finishing wood floors, and cleaning.  

I'll need a roof too.

The larger unit is recently renovated but will require some work to be contracted out (largest thing being dormer out the attic bathroom to make it a true 2nd bath, all the plumbing / tub / toilet is already in place but the ceiling is so low due to the angle of the roof that is it silly) and some HVAC work needs to be done (adding central air and replace one of the furnaces) - we are guesstimating $50k up front for all the contracted work which we plan to finance.We are doing 20% conventional 30 year mortgage, purchase price $315,000, monthly payments will be $1750 a month.  

Apparently refi's and owner-occ business is going through the roof so everyone - especially the appraisers are having trouble keeping up.  

Rent  $1400/month covers these items (as in your tenant)P&I Payment $500.00 Repairs Needed $0.00Taxes $118.92Insurance $208.33Management $182.00TOTAL ~ $1010/month x 5 = $5050Reserves to set aside (emergency - covers 5 months) $5098.33 Expenses Headache Factor=0% CAPEX  $70.00 General Maintenance  $83.33 Utilities 0 0 HOA Fees 0 0 Flood Insurance 0 0 Vacancy  $112.00TOTAL ~ $265/month of useless compensation (using this method) ~ $3200/year Seriously, if you have vacancy due to a repair issue (like a roof problem).  

I already made the decision to go with the dark green roof, and while I don't think I would ever go with that color again, I have to paint the house anyway, so I have to come up with a color scheme anyway to match the roof.