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I wouldn't know the areas to look out for or to stay away from so any advice would be awesome!

Great to hear you had a plan, stuck to it, and executed it consistently.You've made the shift to the "I" quadrant, while your working friends wish to stay in the "E" or "S" quadrantsWhat are the plans now with your new FREEDOM?

Markets stay flat for five years and you've been bleeding cash then what?

I have not received any feedback regarding that, but I like to imagine it does provide a new level of coziness upon their stay. 

Single night stays in a crowed city are a guarantee for a party.

I know if I stay consistent, something will drop.  

Does anyone know if there is any flexibility here, including if I can keep the HELOC if I have had it for 12 months (so stayed in the Primary Residence for a year after the HELOC started)?

And personally, I stay away from OH because it's what herd think has long been and I worry how much of price is based on herd-actions or market metrics.