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If the home is outdated and needing repairs, could a lease option strategy work?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

Make your current properties better such that you will have less repairs later or you can defer repairs when times are not good.4) Self manage your properties if you can.