Ultimately, it's up to you and your personal comfort.

You also want to see a reserve study and only invest in a property where the HOA is at least 30% funded, less than that is assessment territory. 

Use tools like AirDNA or Mashvisor to provide market data on projected rental income and occupancy rates, and make sure your lender works with appraisers familiar with short-term rentals.

@Ezra Avery you might want to read below to understand Classes of Property/Tenants.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I took a small private loan and bought my first home.

I hold a w-2 job currently and considering transitioning to holding some properties.

I found a property in my area that would produce decent cash flow and appreciation; however, I would have to use funds from a HELOC on a different rental property for the down payment.

Ask if you title company can do a double closing and if they know what assignment of contract is.

I have built and bought a lot of them. 

I’m considering tapping into this equity to fund future fix-and-flip projects or even purchase another rental property.My questions are:Do you think leveraging the equity in my properties is a smart move for real estate investments?