At one point I talked to my financially advisor and he said that it would be smart for me to open a HELOC on the property, but not draw from it, except in the case of emergencies.  

Using equity can be a smart way to expand your portfolio, but it doesn't have to mean over-leveraging or creating unnecessary risk.

@Kevin Connauton, I agree with you that although Pad Split is a great choice for getting the rooms filled, they don't cover all your bases in terms of property management.

It’s not a binary on/off choice.

Aloha Joshua,  I deal with clouded/messy titles often and it's not my first choice as its froth with a lot of time, costs and risks. 

Starting with deal evaluation is a smart first step.

If you're pretty smart with this stuff, I think can definitely make sense for you two to talk with a tax planner.

@Ajay Bodas I have heard the same recommendation from my 1031 Intermediary and tax guy, but they both also said, "It Depends"... following this post to see what some other smart members know!

@Franklin PerezGetting your real estate license can be a smart move if you want MLS access, networking opportunities, and savings on commissions, but it comes with costs and disclosure requirements.

A smart seller/listing agent will likely require a large EMD to tie you to performing on your offer, so be prepared for that.