I have read many books and articles on the subject, but I'd like to hear some perspectives from others who have already started their investment journey: when you thought you were all prepared and put your plans into action, what unexpected and/or difficult issue(s) came up?

Another option would be to tell them you have to make decisions based on your investors best interests.Your investing partner could be your significant other, but they don't have to know that.That way if difficult decisions have to be made in the future the frustration would be at "the investor" and not directly at you.

But there are many different personal factors that you would want to consider, which may make it difficult to get helpful answers on here

I'm having a very difficult time finding qualified tenants. 

Their website terms & conditions include giving them the ability to kick someone out of the course without refund for “being difficult to work with” 😂 are you serious?

Oceanfront homes are extremely limited and commonly ask $1.6M+-$2M++ in the center of town it can be very difficult to secure an STR permit due to saturation (active neighboring vacation rentals) requirements.Lincoln City offers a variety of oceanfront home options, the challenge with oceanfront STR's in Lincoln County is that actively licensed STR's do not transfer and would generally be subject to a lengthy waitlist.

The biggest hurdle right now is interest rates, it is extremely difficult to buy in a popular market and actually make a profit out of the gate.  

ADUs or carriage houses are well supported in adjacent downtown neighborhoods but no one is building and selling new construction homes the comparable will be very limited. the appraisal will be difficult. it's just a lot.

@Greg R.It cam be difficult to be at the top of the searches on both AirBNB and VRBO at the same time, because both availability given to the platform and previous bookings on the platform are big factors in the algorithms used to elevate placement.

This has been my first year having a rental and I have been managing it from another state since I moved back to Oregon, which has been difficult and a bit more costly since I am not local.