I think it really depends on which is going to have a greater financial impact, and that is different for everyone.

Keep in mind that HOA’s can completely change the rules and impact your ability to make money with your unit, plus assess you as a member of the class for things totally unrelated to your unit.  

Cash out Refinance doesn't impact things. 

This is creating a lot of opportunity for us by putting skilled workers into the labor force who otherwise would have never left their cushy state jobs.As for other perks....We aren't at the level of being able to offer health insurance unfortunately.   

Before you make a claim ask your insurance guy what impact putting a claim on your STR will be.  

I graduated from the University of Kentucky in 2018 and now I'm currently in the Air Force stationed in Clovis, NM where my wife and I just bought our first home. 

In the large multi-family, if a few units have problems, your financial picture is only impacted 2-3%.

@Varun Maker one factor to consider if you take a HELOC is the impact it can have on your credit score.

Don't leverage everything you have to force the next deal. 

Market driven appreciation is very subjective as opposed to forced appreciation through rent bumps and improving NOI.