Whether or not they ought to be doing exactly that is highly debated.

I have also debated on contacting my agent with all of my information and asking how much he will be charging..... or is that not a good thing to do?

What is the volume or pricing, that is going to be debatable. 

-Debt: $50k student loans, interest rate will be a lot lower than inflation-Tax Flling Status: singleCurrent assets:$25K in emergency funds (enough for at least 6 months of expenses)$75k in VWRL (Vanguard FTSE All-World UCITS ETF)$400k in cashI’m debating myself about the following options:1.

Yes there are exceptions sometimes you get lucky or you have a CA prop 13 type situation where property taxes are locked in at the lower assessed value but the main debate isn't around taxes. 

I’ve been holding since well before the peek in 2017 (🤦🏻‍♀️ should have sold) and have been debating what my next steps will be with my portfolio now that it’s starting to bounce back a little.

I am debating selling my old primary home.

This isn't debate club where you get points for time spent at the podium, move on and find a new LO.That being said, I do not have the full file in front of me, if your day-job was less than 2 years old and not full time, my answer would be quite different. 

As a remote (work from home) employee like myself, my friends and I had a debate about the impact of remote jobs on different markets for real estate.The trend of remote work is growing quickly and I have heard many of my co-workers moving back to where they grew up versus Boston because of the cost of living.One big reason for people living in big cities besides the experience factor, is employment.

I've debated on looking into multifamily units, staying in one renting another out, buying a 'cheaper' condo ~500k, or investing out of states.