I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

HUD does not factor into the rent other amenities that might be included in the rent such as garage, basement, fieplace, central air, pool etc, that might command higher rent in the non-Section 8 market place. 

And that's the fact that the main entry point from an intrinsic standpoint on RE was during the outlier period.Real estate is not an intrinsic day 1 asset.

I am experiencing similar issues with time of year being the main culprit.

It's in on a Main St in an small town in NJ.

In your situation there is actually another factor that may work in your favor.Only the proceeds allocated to the sale of the building can be used in a 1031exchange. 

This focus gives you a national reach, and that oh-so-important factor; scalability. 

What you paid for it and invested in its upkeep are not factors for pricing/selling a property. 

Principal balance currently at 314kProperty Details: It's essentially a "2-in-1" property, with the main unit rented out for $1,900/month and an attached ADU bringing in an additional $1,200/month.

If it had been my client buying this property, they would have paid a lot less even with the full commission factored in.