This is one major reason I always caution people about going with big national marketing companies who don't actually live and work in the markets they sell....but I digress. 

If it isn’t clearly on your property, you shouldn’t have to pay for it bit I’d also weigh the risk of having it fall and doing major damage versus just chipping in a bit to get it handled before any damage is done.

If you do not know what you are doing I would strongly recommend hiring a lawyer and be pro active in removing this person from your property.I believe you are facing a major problem, I could be wrong, but I would not take the chance if lying on your application is grounds to evict.

So, like I said, if you've found your "forever home" and want to lock in interest, have someone else pay down the majority of your mortgage, etc. then I think it's a viable strategy.Just realize you're buying for "want" and "emotion" and you'll be fine. 

If you're looking for either land to build on, a tear down, or a major fixer upper, where do you look besides the MLS and craigslist?

I would say your major challenge right now is being able to find someone who has enough free time during busy season to start that conversation with you and onboard you as a new client.  

That might make your rental noncompetitive after a major investment, especially in cold climate areas.

Charlotte is becoming an increasingly expensive area to buy in so I would imagine that the majority of places worth buying are probably too expensive to cashflow.

Typically, if people don't want to list on MLS during a seller's market, it means either the property is not likely to qualify for traditional financing, which could work in your favor, or they want more than the property is actually worth and can't find an agent to agree on a listing price, which could be a major barrier- you might try to see if you can find this info out.

I highly doubt NYC is the market for you, with that being said there are reasonable priced places within an hour of almost every major city.