If you live in a property as your primary home for 2 out of the last 5 years and you sale it, you do not have to pay taxes on the gain up to $250K for a single person or $500K for a married person. 

., In your situation you would get to take the first $250K of gain ($500K if married) tax free.  

My fiancé (getting married in 3 weeks!) 

My husband and I bought our first home in 2016 before we got married, and it doesn’t have enough equity to sell, and the main reason the guy decided to sell was because he couldn’t get any renters in it.

If a husband and wife file a joint tax return there is no other way to interpret the tax payer being anyone other than both of them by virtue of the joint return.The issue that then crops up is the selling as yourself (one tax return joint married) and buying as a disregarded LLC. 

Later down the road, if you choose to get married and have/adopt kids, you can move into a house and now you have a multi-family property on the side that will continue to make you money.

As a married couple can we file taxes separately and each have our own primary residence? 

So, in this case, you get the best of all worlds - enjoying the most favorable cash flow situation that you can muster (the less you're dipping into the HELOC the better) - but if you pick the right opportunity you will also get the chance to actively manage some value add project(s) to a property that you're already living in.If you're married to your current house and living situation, fine. 

Many times two people will each own property before they get married and not change the deed from individual to joint tenants - sometimes for years. 

We were getting married and starting to think about kids, I knew we'd need a family home and this was the only way we could afford to do so.