DC will require you to have 2 egresses, so you will need another door, or larger windows (with no bars). 

A bird dog looking to meet your requirements and standards!

Should I waive the escrow requirement?

They fall under the $400 SE income threshold for filing and do not require tax returns.

I am looking for populated desirable areas with no rent control laws..

In Florida HOA’s are required to carry policies with replacement cost, Actual value is not allowed by law.

For example in and around DC some jurisdictions charge insane fees for new builds ($40k school impact fee) and have very challenging code requirements (sprinkler systems in homes..)Anything crazy like that?

But it's important to assess your financial status, emergency savings, investments, and cash flow requirements before making a decision.

I explained that i wasnt going to pay for it and she told me that her understanding was that if it was physically part of her unit and provided by me that I was required to service it. 

There only job is to keep track of the funds and create the required paperwork for the IRS.