Short answer:  a sewer scope is ALWAYS worth it.A couple hundred bucks to potentially save yourself tens of thousands, and weeks or months of lost time and vacancy?

I can't speak about if HOA fees affect home prices, so much as I can mention that some buyers specifically look for no-HOA properties, or must factor in the HOA fee when deciding what monthly mortgage payment they can afford.If a buyer's finances are tight enough that the HOA fees make them question if they can afford the property, then they're probably not the right buyers.Some of my buyer clients just want to be in xyz neighborhood, and the HOA fee is just one of those things they know comes with the territory.I serve Pinehurst, NC, which is internationally known as a mecca for Golf enthusiasts. 

Should I keep it or rent it out unfurnished (w/ management I will cut even or loose like $100 per month cash flow)? 

suggest you start with Dave Ramsey principals ... then move out from there.there is some big huge fallacy  that Real estate is going to let you quit your job and your going to have all this time for the kiddos etc.this will never happen in the short term with rental property.. you build a nice base for retirement in 30 plus years for sure.. but for short term replace your income and have all this free time you need to make transactional income with big hits.. your not going to get their with 200 to 300 a month cash flow on a levered up rental . 

Today I invest passively in real estate, putting small amounts ($5K) in different passive investments (such as syndications and notes) each month through an investment club.

Just did it two months ago.

I am fourth generation for a family owned management/development/consulting company based in Southern California but I am in Idaho for college around 9 months out of the year.

Buy and hold in Hawaii doesn't usually pan out unless you're willing to go negative monthly (often considerably) to maybe gain some appreciation over time.

Everyone finds the rooms too small or something that does not fit their family,etc.I am at the point of breaking even but in a month I will be losing money because of the Hard Money lender payments.

Also, in this hot buying market for the last three years, I only need the first month and my listing pictures.