The current Chicago market is so dry and overpriced it’s ridiculous, mix that with the rising taxes it’s making me think twice about purchasing another property here until our politicians stop robbing us.

You don't want to have expectations of demand that dry up when a recession hits. 

Due to restrictive covenants placed by lenders on other parcels, he’s unable to pay interest in excess of 9.99%We purchased the said parcel (valued at $4.6million for $2.5million, with the seller having a 7 month option to repurchase the tract for $2.975 million.

Some lenders have "float downs," but typically these are lenders with high "starting" rates to begin with, they're just cutting into excess profit they normally collect, it's not actually a float down even though it appears that your pricing gets better.So if you're getting a good rate, expect not to be able to float it down.

Excess heat and condensation can cause major damage to your roof and roofing materials."

I find the additional protection excessive if you own, let's say 5 duplexes all with liability insurance policies on them.

Excessive candle burning.....

We still have plenty of dry powder to put to work and like you are continuing to look for off-market deals, we have a number of LOIs out but as you know the demand for this asset type is growing, pricing is pretty rich and it's often hard to convince owners to sell.  

Only Tier 3 requires annual inspections because it "requires excessive city services, poorly maintained or managed, may be at a higher risk for fire damage". 

Anything excessive could backfire on you and it's what causes tenants to fight you in court rather than move on.