I'm trying to find good STR mgmt companies that would be able to manage a 2 flat in Albany Park and a single apartment in a 20 unit bldg in West Ridge. I'm completely new to this but am an experienced multifamily inve...

As long as you are using a reputable title company - you are in good hands

So, while most syndicators realize the reputation damage will far outweigh the expense reimbursement, it is not guaranteed and theoretically, if the partnership fails to acquire the asset, you could be liable for out of pocket costs, sometimes with interest included.  

This creates an inherent misalignment of interest as the GPs only goal will be to sell the property as soon as possible (so they can cash in on the fee).Also, in this scenario the GP has no incentive for the deal to perform well besides the reputational damage they'll incur with their investors, thus making future deals less likely. 

From looking on a map, didn't see any pet boarding facilities right nearby, and they have a great reputation for the area they serve.  

The bad reputation comes from OOS investors wanting $20k D market properties.

I'm looking for a referral for a reputable AirBnB (short term rental) operator for a unit in Chicago. 

The goal is to offset our water bill each month.2) Are used machines usually reputable?

Any help or suggestions for a reputable insurance company where I can find coverage for that area would be greatly appreciated.

A cost plus or time and material project is a different story which may be a good option for you if you are afraid that you may be overcharged.Get 2 or 3 quotes on the same scope of work from reputable contractors and compare prices that way.