BUT...As it stands, the numbers look damn good to me.

I have a good tenant who has been with me for a year, with the lease set to expire in October.

Good time to reposition into something with no HOA I'm guessing, or sticking with another Condo? 

I have also seen a lot of negative posts on here lately about the real estate industry so just need some assurance this is still a good route to go.This is also one of the first properties I’ve toured so I don’t want to jump too soon but I also don’t want to miss out on a good deal.

If you don't think the up front cost of $30-40-60,000 is worth it, then it is not a good investment.How do you make ROI off solar panels on a house?   

It comes down to the landlord keeping good records and following the laws correctly. 

I need to pay off my HM lender.. so it would either be do a HELOC and keep the property or sell the property take a good 100k profit and pay off HM lender then move on.

Hopefully they decide to stop smoking instead and all is good. 

Knowing the future structure is good and planning is also good, but if you are spending the majority of your time, as it said, on structure and not real estate, your reps are being put in the wrong workout bin.

Good luck!