A relevant consideration when you have a property leased to another closely held entity.

How relevant is that to the conversation?

This has a tremendous impact on cap rate and I read a story where a client had an accepted offer to be used for 1031 exchange, only to find out during due diligence that the listing agent put the lower cap tax value in the listing expenses instead of the actual and relevant current value.

I wasn't connecting with anyone and I wasn't asking questions that were relevant to me to help me in my specific path.

Like Bill said, taxes are the only thing that that your $500k is relevant for.If you factor in 7% closing costs on the sale and 2-3% on the purchase of another property (assuming that's what you would do with the money), you'll end up being able to purchase a place costing about $165k.If you think you can get better returns on your $165k elsewhere or if you are in a high tax bracket and could use a big write-off, then sell.  

Just haven’t been able to find any good institutes and we’re looking for some relevant and experienced responses.

I'm also looking to house hack a multifamily using my VA loan so your experience is especially relevant.

All good advice here, as far as learning what questions to ask, but gather the relevant info there locally before you make a decision.Get referrals, obviously. 

From skimming through they seem to be packed with great information and extremely relevant.

Central Massachusetts Housing Alliance, INC.We own a multifamily in Massachusetts and this book has a lot of good relevant information specific to Massachusetts.