Long time lurker, first time post. Bought a home as my primary residence for 400k in 2008 in UT. I added 65k in improvements, and started renting it out in June 2014 when I moved to NC. My tenant in UT wants to purchase the home for market value which is about 550k in April, I have a mortgage balance of 300k. I think I have 90k in CAP GAINS, if I did the math right. Looking at my options of the 1031, I am not clear on what options there are for me. I am interested in a property (home or condo) vacation rental near beach, mountains, or on a lake that I can personally use. Several questions 1) Do I have to replace like value (550k) in the 1031 or can I do a condo for 250k? 2) Do I have to replace the currently financed amount of ~300. 3) Do I have to do all the transactions within the time frame? For example, 4) Can I buy land with the proceeds for ~250 in the first 45 days, and build a structure with a construction loan and then "term it out" later with a refi? 5) Or, can I buy a 400k home that needs work and put 100k into it? 6) How would you do multiple condos (assuming a total of 550k), 7) should I stop being a land lord and pay the cap gains??? 8) What is the long term strategy to get out of the tax liability, move into the property?