I want to get rolling with investment properties and Jaren's rental academy has been an invaluable resource to me.  

You could sell that and roll the profits into multiple downpayments closer to you so you can start to streamline management better and not pay for it.

That doesn't mean it isn't a good strategy - if the property still produces healthy cash flow after expenses (which includes future capital needs if you've deferred such), at a minimum you could be rolling the cash flow either back into the home to own it outright or using those funds to prepare for your next purchase. 

Sounds like rolling the dice to me .  

Roll back taxes, HOA arrears are just a small sample of undisclosed issues you will face.  

You can fulfill the 1031 requirements so you can roll it into another. 2)Does the baseboards work fine?

If you are also living below your means, saving, and reinvesting after tax dollars you can get the ball rolling faster.Nothing ruins an investing career faster than a surprise $20,000 CapEx bill to a new investor who has $2,000 in the bank and just spent every penny they have on a high risk property. 

So if you have a $20,000 rent roll paid off you can count on taking out 10k.

Roll a dice.

@Ryan DragonThe question is are you happy with the Return on your current equity, and can you roll the equity you have into a better yielding asset.You're generating around $6,000 per year in cash flow, but how much equity would you have if you sold?