In Milwaukee, I'd need 2 exits from the attic and 50% of the space has to have at least a 7 foot height on ceilings.Two things you want to check: both requirements are correct, but on top of that the city is getting reluctant permitting 3rd units: 50% more occupants mean 50% more water and sewer and 50% more traffic and parking.The other issue is that the cost of finishing a thrid floor with proper insulation/ventilation will run about $50-60/sf and only makes sense if you can get strong rents. 

How are you going to get the rehab completed and can you correctly estimate how much a project is going to cost?

@Dan Heuschele, sounds like you got your answer, but over 5 years of actively working with over 4,000 LPs, my experience aligns with Brian's.I am sure, as of today, the number of LPs that want out of deals going south is probably much higher than leading into this correction, but unfortunately, if you want out after there is already a scent of blood, the chances of finding a willing buyer at anything more than pennies on the dollar is probably slim to none.That being said, I know Cadre runs their own secondaries platform.  

Your thought process on the contractor providing quotes to possibly "win" a job may seem correct on surface level as a lot of businesses offer "free-mium" products - but ultimately time is money, especially in real estate where good contractors are in high demand and could better spend their time finishing a project before accepting the next one. 

Can someone point me to the correct forum subcategory to post these to as well?

Correct.

Verifying rental history often takes a long time tocomplete due to applicants not giving us correct landlord contact information, landlords not returning our callsor refusing to give us any details.We also deal with applicants trying to have family or friends pose as theirlandlords.

So if I understand correctly, you are saying that - even when rented, you will have a negative cash flow of $3k a month?

@Igor Balakhnin pretty sure @Bill Brandt is correct.

What matters is that you have more knowledge about an area than your competition and you have the correct team established.