I've been under contract to purchase a 2 flat in the Jeff/Portage Park neighborhood of Chicago, it was a not approved short sale (we have now received approval, we have 30 days from today to close)

It's a standard 2 unit masonry home, with finished basement with an illegal unit, and a recently renovated one unit, other has original finishes w/ new carpet. ~1000 sqft each unit 2br 1ba. (Market rents are conservative $1150 for original finishes unit, and $1300 for a recently renovated, garden unit (let's assume I will be living in and not renting out for a $1000 market rent that it can attain)

The purchase price is 335k with a 3% closing cost credit. (decent deal in a HOT Chicago market) but the home comes with some violations from the prior owner, they are 10 and 5-year-old violations, my attorney believes should not hold up closing, my mortgage broker has a different opinion. the total to cure violations is about ~30k-40k

My lender misleads me from the beginning of the transaction, leading me to believe I can purchase the property with conventional financing and 10% down, he knew the property had violations. (we've been waiting for approval for 4 months) I could've come up with extra cash had I known, I'd need a minimum of 15%... which is really upsetting, however since being surprised by this, one of my family members volunteered to bridge the 5% gap in financing I'm missing. (I'm very fortunate)

At this point, my lender told me I'll need ~80k for conventional financing, (50k for downpayment and 30k to fund the violations repairs upfront), or go with his 203k loan (which will take longer the 30 days that the bank allowed us to get approved) I'm not sure whether to believe him or not, since he mislead me from the beginning.

Neither scenario is ideal, my original plan was to purchase the property and fund the repairs over a year-two years time, while I live there.

Some of the violations are TLC and easy fixes, other like the deck might require full replacements (I've been quoted 15k)

WHAT WOULD YOU PRO's DO? (Thank you in advance)

Here's the violations list:

CN062024	Failed to maintain parapet wall in good repair and free from cracks and defects. (13-196-530 and 13-196-641)	North and South parapets , spalled bricks and loose mortar with ajar mortar joints .
CN063014	Failed to maintain chimney in safe and sound working condition. (13-196-590, 13-196-530(b) and (c), 13-196-641)	North chimney spalled bricks and loose mortar with ajar mortar joints .
CN069014	Failed to maintain foundation in sound condition and repair and so it adequately supports the building at all points. (13-196-530, 13-196-530(a), 13-196-641)	Rear basement areaway , peeling masonry coating on foundation walls .
CN070024	Failed to repair or replace defective or missing members of porch system. (13-196-570, 13-196-641)	Rear two story wood back porch requires replacement with plans and permits . All components rotted with worn finish .Unknown foundation status , with uprights set on blocks and wood. Uprights twisted and notched . Beams rotted through, overspanned and only nailed to columns . Joist overspanned and undersized , not on 16 on center . Decking rotted/loose . Stair stingers no support . Stringers cut too thin .Stringers only nailed to columns . Winder stairs don't have support . Guardrails are weak and loose , overspanned and only 36 inch tall.
CN073014	Failed to maintain exterior door in sound condition and repair. (13-196-550(d) and (e), 13-196-641)	Front entry door frame rotted, with flaking paint and worn finish .
CN077014	Failed to maintain fence in good condition and repair. (7-28-060, 13-196-630, 13-196-641)	Rear wood fence and gates, rotted, leaning and loose with worn off finish . Fence over five foot high requires permit.
CN079014	Failed to maintain garage in sound condition and repair. (13-196-530, 13-196-641)	Rear garage - has rotted windows with peeling paint and putty. Service door rotted, needs replacement . Trim rotted with flaking and peeling paint .
CN138106	Remove and stop nuisance. (7-28-060)	Front and rear yards , high weeds and overgrown shrubs .
CN190019	Arrange for inspection of premises. (13-12-100)	Interior of Building - No response , unverified detectors , conditions and occupancy . No entry basement conversion complaint .
CN196029	Post name, address, and telephone of owner, owner's agent for managing, controlling or collecting rents, and any other person managing or controlling building conspicuously where accessible or visible to public way. (13-12-030)	Building - No owner's I.D. sign posted .