I've paid off a mortgage twice now. Both felt great but were fairly uneventful...call the bank to get the payoff amount and move the money online. We live in a very LCOL area so houses are relatively cheap.
The first time I bought a fixer upper for 60K. We put down a large down payment 20K and put my wife's entire (crappy LCOL 1st and 2nd year teacher's) paycheck on the house every month because we knew she would stop working when we had kids. We were 24 when we had it paid off.
About 5 years later we sold the house for 110K and bought another for 145K. We didn't have enough cash to comfortably cover the gap so we had to go to the bank and "try" to get a mortgage. I went to 3 or 4 banks and all of the conversations with the loan officer were somewhat awkward and went like this:
Me: I need a mortgage.
LO: mmK, and how much is the purchase price of the house?
Me: 145K
LO: mmK, and do you currently own a home.
Me: Yes, well, no...kinda...it's sale pending.
LO: mmK, and what is the selling price?
Me: 110K
LO: mmk, and how much equity do you have in that home?
Me: All of it.
LO: No, I mean what is your current mortgage balance?
Me: No mortgage.
LO: Really? Well, that makes things easy. How much are you wanting to borrow?
Me: About 35K
LO: And for how long....I assume you don't want a 30 year.
Me: Do you have 5 year mortgages?
LO: No, the shortest we can do is 9 so we can sell the mortgage.
Me: I'll have one of those.
Two years later we paid of the the 9 year mortgage.
No regrets.