He could delay important repairs and not do them to make the financial statements look better. 

I want to remove my bias here, so I will stick to the facts:Home had foundation repairs done in 2008 and 2012Seller had a 3rd party engineer do a class C foundation inspection on 3.20.2018 and provided the following:Overall elevation differential of 4.1 inches.  

Rehab Costs Total Rehab Costs ($110,000.00) Total ($110,000.00)After Repair Value $575,000.00When I look at your report all the estimated repairs lines just say "N/A. "  So are you just guessing?

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.