I would check the RLTO on the first item, that may not be allowed in Chicago.The refusing entry is addressed in the RLTO and the summary has to be included with every lease.If you are owner occupied under 6 units you are exempt from the RLTO but I always suggest every landlord use a RLTO compliant lease like the 35 page CAR one that includes everything you need

Helps if someone should try to stiff you.Depending on your clientele, you might want to include a page with a description of the condition of the apartment and/or photos, and have them initial and date each item / photo at move in.

People see these advertising items, and think there is a quick solution to their problem.

This is my 1st time with 1040 and rental.a) Is it possible to list the closing costs under any expense item - eg. commission.

In what you have described the only issue I can see the underwriter asking about is the derogatory items from 2010.Relax and breath.

If you're knocking it down and building up on the existing foundation, you may be grandfathered in on some items.

Welcome Sam, I like the sound of your business model.  

Do you think you can ask for the seller to repair those items as part of the negotiation process?

I've used Quickbooks and Peachtree in the past.....Xero is a much easier product to use and actually allows you to calculate depreciation each month (which last I checked Quickbooks does not do).I set up each rental as a separate "project" so when preparing tax returns on the Single Member LLC, I can easily split out the Schedule E items.

Personally, yes, I think wholesaling is a very difficult model in coastal california.