I own an older house that's in decent shape but needs some renovations including adding dormer to our attic (or just raise the entire roof possibly depending on expense) to facilitate a closet and more headroom creating an actual bedroom. 

On the side, for the past 12+ years, I've been a hammer-swinger for the two residences I own, doing literally everything except roofing (yep, everything, including plumbing, electrical, ductwork, flooring, demolition, framing, drywall, brick-laying, windows, cabinets...... etc).

Limited is a max of 35k in repairs, nothing structural is allowed to be done (you can replace the roof put in a new kitchen, but you cant repair a foundation or cut a hole for a new window for example).   

I'd have to run sewer and all utilities to it, as well as do a studs down remodel (it actually has good bones and a reletively newer asphalt shingle roof). 

Correction:  Roofing question...strip the old or roll right over with new?

I have the cash for a new roof but would rather not pay the expense. 

Please note, this includes: the roof, plumbing, electrical, HVAC, kitchen, etc.We had another set of contractors who gave us a quote $130,000.

I already walked through the property and the only thing I could see is that it definitely needs a new roof, and it has water stains on the ceilings, so I am going to estimate for cosmetics and other repairs around $32,000 max for the interior and exterior updates.

JeffListing Price:$159,000 INCOMERental Income$1,748 $.85/sqft.Garage$0 Laundry$0 Storage$0 Misc$0 Total Monthly Income$1,748 EXPENSESTaxes, Property$350 Insurance$100 UtilitiesElectric$0 Water$100 Sewer$50 Gas$0 Garbage$0 HOA$0 Lawn/Snow$0 Vacancy$100 Repairs$100 "Capital Expenditures (i.e. new roof)"$150 Property Mgr $0 Mortgage $705 Total Monthly Expenses $1,655 CASH FLOWIncome $1,748 Expenses ($1,655)Total Monthly Cashflow $93 CASH-ON-CASH ROIDown Payment $15,900 10%Closing Costs $5,000 Rehab Budget$5,000 Misc, Other  $0 Total Investment $25,900 Annual Cashflow $1,111 Cash to Start: $25,900 Cash-on-Cash ROI 4.29%

Damage runs the gamut from a few trees down at one property to a roof completely gone off of a triplex.