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I've never accepted money from her, never officially acknowledged her as a tenant in any way, but this is NJ where getting rid of a tenant is notoriously difficult.

Staying current on market changes, possessing the experience to structure the offer that a seller will accept is very valuable!

It seems like in the areas I've been scoping out that there is decent acceptance of STRs in condo complexes, but it definitely will take some additional work w/the RE agent to make sure.All of your points about managing and having the maintenance handled by someone else is SUPER attractive. 

Some, such as Edna, accept investor money from their students. 

@Luke Hoffman your insurance carrier would like to see you request $300k, but most will accept $100k.  

Someone else will accept even more negative cash flow?

@Gustavo Zamora, you are correct that sometimes the terms of a deal (type of financing, seller assist, inspections, etc) can affect whether a seller accepts your offer or not.

If you are not using a lender then you can accept the title with defects.

You could ask them what they need from you to provide more information and ask what information they will provide if you give them what they are asking for.For example, a lot of realtors will not provide much info until a PA is submitted and accepted along with proof of funds.