Ok, let me first state that the math clearly...overwhelmingly says to sell, but here is my dilemma. I love living on the water, I searched and searched for years to find the perfect spot in the area I live in that is filled with awesome lakes. Along comes the housing crash and then the financial crash, I timed things perfectly and bought a home with cash at the absolute bottom out of foreclosure. It is in the perfect spot, 1 acre on a peninsula, postcard perfect sunsets, close to all my friends, centrally located to bike trails, and local fun activities. The rub is I love the location, and the house is spectacular, but its WAY too big for just me. It is a relatively HCOLA, now if I would want to "downsize" the stuff available that is smaller, is not in the nice areas I'd want to be, and in my opinion way overpriced (which maybe my place is now too).
I can totally afford the home and its ongoing expenses. They are included in my budget and I've been FIRE'd for a couple of years at less than 2% withdraw rate with my paid for home not included in my net worth calculation for that. Like a lot of places around the country there has been significant appreciation from 2011 and now with $900k to $1M appreciation on the place I sort of feel irresponsible not taking the chips off the table and having a more appropriate sized place to call home (like 1/4 the size). The struggle is I don't need more chips and there really isn't another place I am desiring to go, but when I walk through my overall picture I think damn, I could cut bat pay the cap gains tax, add the already "enough" stache and go rent someplace for a while and wait for the next inevitable cycle to repeat. Hell, the proceeds from the house sale would make my withdraw rate well under 1%. I realize this is a first world issue, but just curious if any of you sage real estate investors would like to chime in.