Ultimately, it comes down to your strategy and how much you aim to scale. 

Seriously considering but I need boots on the ground to service correctly.

It's just the AC and some deferred maintenance that it really needs.  

To top it off when I told them they need to pay for 1 day they’re staying over they have ignored my messages.

I will love to network now and offer my help as well to anyone who needs it.

You'll do so much more in a team.  

KowalIf this is true a sound strategy is to get bonus depreciation to get as much loss as possible (which gets to reduce my pension income) and as much sec1231 gain (which becomes cap gain)

What do I need to learn?

Any info you may regarding Investment property HELOCs would be much appreciated. 

Down payment can be higher than primary, but the good thing is that you won't need that much income to qualify because lenders can you 75% of the market rents for the units of the property.