I don't know the area at all.

Pretty confusing area!!

The key is to find the area(s) that have both limited regulations and an abundance of attractions.

I'm a licensed real estate salesperson and investor who owns some single family houses in an area that attracts people seeking vacation properties, but is not very densely populated. 

I am a General Contractor working primarily in the Philadelphia and South Jersey areas.

Unfortunately you cannot check New York eviction records and they are the best predictor of future problems.

If it's been listed for 100 days, do you think other investors in the area are keeping an eye on it?

Very few places in BR that I'm aware of will bring over $2k/month for a 1200sqft 3/2 and those are A/B neighborhoods with $250k+ ARVs.

Dont know your area 

You’re right, I’m trying to use the expenses to offset my W2 income, there are indeed some grey areas on what time counts and what don’t so I’m trying to figure that out as I log my time.