We jumped into a new market and also into a new asset class (mid sized multis) in the last year and it has been great, we have bought a 12/19 and a 32 unit the knowledge I have gained has been amazing. 

Or you can sell it down the road (after 2+ years) and pay zero capital gain tax. 

We just got an offer accepted on a Condo on Kauai and our next move is to purchase a multi family in the Beaverton, OR area.I’m hoping to network and gain valuable insight from this forum as well as provide any personal success and challenge experience from the standpoint of an active duty military member who has purchased and sold multiple homes.

I would start now by trying to get on as many wholesaler and broker email lists as possible for deal flow, and possibly getting licensed to gain access to the MLS, at the very least for comp analysis.

Capital gain would be the sale price (less) your basis And you can sell this and defer gains via a Qualified Opportunity Zone. 

And then f the HOA fees are ridiculous, then selling it capital gains tax free who save you money in the long run, more than making up the legal fees.

We’re not sure if this is the right move, as we would lose the additional monthly income from the rents, and also any equity the house may gain in the future, if we choose to wait to sell. 

(Particularly in Mid-Hudson Valley of NY if that makes a difference for licensing, etc.)I don’t want to cross any boundaries with my first post, but I’m trying to gain a foundation of knowledge to help my family unload some inherited land.

One of the biggest pros is the knowledge you will gain and possibly the networking. 

Now I'm not a CPA or tax attorney so this is just my understanding, please consult with appropriate professionals but if you were to live in it as your primary residence than you should be exclude from long-term capital gains up to $500K  (for a couple) of profit when you go to sell it, not sure what your intention was on length of time that you two would live there or desire to sell it down the road.