just because the house is 1/10th the cost doesn't mean the repairs will be 1/10th as expensive. 

Get an estimate on the repair. 

This property has the potential to be a cash flow machine.Now I’m sitting here the next morning after looking at the property arguing in my own head whether or not I should just go ahead and make an offer and for how much.

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.. 

However, after detailed conversation with Tammy, I decided to trust my heart and go ahead!

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.

If you go the route of self-manage, do it ahead of time and YOU synch the rental company calendar with your calendar.

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If the home is outdated and needing repairs, could a lease option strategy work?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