Get an estimate on the repair. 

Don't cut your expenses short or repairs short.

If you buy and renovate I would try to find a Private Lender if she does not want finance that would include the funds for the repairs/rehab.. 

Cicero rental property owners/investors, Please share your insight on this dealI have 4700 W 20th St Cicero under contract for $245,000- 2 units: 2 bed 1 bath + 11x6 sunroom- 2 units 2 bed 1 bath + small porch- 1 garden unit (studio) -1 central radiator system, Hardwood throughout, Seller is making Cicero repairs. - 1 unit needs new kitchen & new toilet & vanity & 1 wall of drywall.- Windows are oigional with old aluminum storm windows some are broken.4700 W 20th stMarket rate (conservative est) Market ratePainted, StainlessAll rentedcompetitivly priced including basement1st floor Front 2bd 1ba includes front porch9009009001st floor 2bd 1ba with heated sunroom 6'11"x 11'9009009002nd floor 2bd 1ba + front porchKitchen needs floor sanded, cabinets plaster, paintBath needs toilet & vanityPorch needs drainage8758752nt floor 2bed, 1 bath heated sunroom 6'11"x 11'900900900Basement STUDIOEgress windowsdrywall, 1 wall needs fixing500Garage$120$150$150Mortgage 260 for 3 units270 for 4 units280 for 5 units-$1,248-$1,296-$1,344heat (heat & cooking)-350-350-350Tax-$635-$635-$635Water & Garb-300-300-300Insurance-$145-$145-$162ElectenanttenanttenantUnits Rented3 units4 units 5 unitsMonthly Cashflow$142$999$1,434If this were 2016, I know I would be overpaying.

All things being equal as holding will eventually need repairs on homes etc.

If the home is outdated and needing repairs, could a lease option strategy work? 

If not, you might have to negotiate the repairs will need to be done prior to closing.

I am really not too sure that I calculated closing costs or repair costs accurately.

The only negative I can think of is that the current Owner possibly may be deferring maintenance expenses or any repairs or replacements to make his/hers expenses look better along with the bottom line. 

The repairs were estimated at $250k, which included completely redoing everything and building the addition.