It depends...

@Sejin Kim, I think it depends on how negative the cash-flow is.

Depending on your goals, keeping the wedding venue and continually letting it appreciate while increasing the cash flow of that property if you moved and rented the cottage.

Depending on what the smell actually is, I use kilz restore primer and then paint the place.

As for specific: do this, don't do that, it tends to be market dependent and/or unit condition specific.  

I do understand that it depends on my markets and other factors but would like having some benchmark to help decide a good or great deal from a bad one.Also, to get to the $3k cash flow, how big a house would it require?  

I think this will really depend on your risk tolerance and honestly sometimes opportunity just falls in your lap. 

Also depending on your state, if it is a buyer beware state that will make it that much harder.

Or you can refi as two separate condos, or as a duplex depending on what fits your needs, or maybe you sell both off eventually, but having the flexibility to exit and a couple different ways allows you to pivot based on outside forces.  

I would say it depends on your market median home prices and other considerations.