In addition, myself and another investor host a real estate meetup every month in Worcester @ the hangover pub.

You get that big hangover from Thanksgiving, everyone's stressed out trying to find the perfect present, sick of all the pushing and shoving at the mall and the Amazon guy is a day or two late on everything. 

Those who doubt that simply haven't done their homework.out this way we plowed through the hangover sudivisions years ago.. 

The branches of the tree hang over my tenants parking spots and they have complained that smaller branches have fallen and scratched their car, as well as a larger branch falling and taking out a section of fencing.

Did not even have branches ever hang over the structures. 

I don't know if you mean this to be an STR or LTR (I am not familiar with Oahu rents but >$3k/unit that close to the beach does not seem outrageous to me), but if an STR, I wouldn't do it at the current time - Hawaii is too likely to suffer from the Covid-induced hangover for air travel that could impact tourism there for months or even years.  

Why is there a popular sentiment that the 2020 recession is just like 2008 where there will be a major housing correction? First off wasn’t 2008 simply an outcome of poor underwriting and loose lending standards which...

If you are going to be there 3-5 years more, you can do small jobs around the house to fix it up while saving more money and paying down the debt.I am a big fan of paying off the debt as soon as you can so it doesn't hang over your head.

They are currently upside down in their residence (2007 hangover) and this will give them the flexibility they so desperately need. 

If you don't do it, it will hang over you and ruin the rest of you day.