I'm getting married in the next year and starting a family, and we plan to move out when that happens, which means that even if I went through the permitting process now and was granted a rental permit w/the town, I knew that ultimately I was going to find myself screwed when the time came to get a renewal on it (every 2 years), and I wasn't able to prove that the property was still owner-occupied.

My wife and I purchased our current home 5 yrs ago before we were married.

(Nothing worse than being married to a relationship that you have not experienced yet). 

Your interest in it, your goals, your objectives will find the people to marry yourself with to get deals done.

We were married recently, and when we add in our wedding gifts with what we have been saving on our own for years, we feel that we are finally ready to pull the trigger on our first property purchase.We actually live about 90 minutes south of the ski area that we are looking to invest in, but it is an area that I am very familiar with as I have been going there my whole life.

Option 2: I can sell it and pull all the equity tax free, since I'm married and it's our primary residence.

The reality is many of these are not deals because the sellers will not do subto.Its like asking a married person to marry you and leave their spouse.

The SMLLC was treated as a disregarded entity for tax purposes (married filing jointly). 

If you lived in your primary residence for the last 2 years of 5 years, you're eligible to sell it and pay no taxes on the first $250K for a single person or $500K for a married couple.

Contribute to your HSAIf you are married, you can do 2 & 3 double.