Having one nearby so that you can manage it better means that you will spend more time cleaning and maintaining rather than hiring someone else to do it and thereby get host burnout in a few months time.

Generally speaking, have any of you invested in this area and been successful?

From what I've seen in this area right now, it seems like you'd have a hard time paying market LTR rents and making a good spread. 

What accumulated knowledge will you be able to leverage for more successful investing?

He told me he owned a few mobile home parks in town (they were large and had high lot fees) and this is what sparked my curiosity.

Quote from @Lee Banks: Hi my name is Lee I'm looking too buy my first rental property and but I feel as if I need a mentor to watch, I still need to learn the basics of real-estate does anyone in New York do programs or mentorships and where would you start if you first started real-estate today  Hello Lee,I'd recommend looking up local meetups here on BP, meetup.com and, eventbrite.You can also call around to speak with RE investors and professionals in your target market to begin making connections.With so much available information online, I'd recommend speaking to a few people and doing independent research before committing to mentorships.

The adjuster will dig into the details.

To rope in possible investors, you must inspire confidence.

Is there supposed to be some "problem" we are looking for in this?

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.