I am currently about 4 years away from having my house all paid off. I bought the house in '05 for $265,000. There are no real comps available in my area right now and I have been told to expect $450-$495K by several real estate agents I have spoken to. I was thinking more like $435k, but I know a couple of the agents personally and they have no reason to lie to me as they know I will not be using them for the listing.

So here comes the question, I am considering buying a $525k house, then selling mine vs selling mine, then buying. My reasoning is that uninhabited houses sell better, they are easier to show and I can buy the other house that I want right now and have a few months to get the old house sale ready. This would likely involve a Home Equity Line of Credit or Home Equity Loan. This would also remove the need to store our possessions or find a shot term rental. The downside I see is being stuck with 2 mortgages. The market around me is hot, especially 5+acre panels like mine, but there is no guarantee.

How would you proceed?

TLDR...Buy a new house before selling the old one?

ETA...Already have pre-approval from the bank for $510k on top of my current mortgage.

Obviously, you can afford it.    Just get the sale done quick.    Don’t get caught with your pants down in the next downturn.    It happens quick.  - It could already be happing.    How long can you afford to keep both houses?

I wouldn't based on my personal opinion but, consider a bridge loan using the equity in your current investment.
No matter how you decide to proceed with the purchase prior to selling your current home, there will be far more risk. Another avenue to consider is to put your home on the market and make an offer contingent on your existing selling. If the buyer accepts with a "bump clause"(you'll have 24-48 hours to remove contingency prior to the buyer accepting the other offer) and you have x time to remove your contingency have your bridge loan in order and ready to proceed.

Edit - If the buyer accepts your offer without a bump clause then it's a win and the seller of the home has a shitty Realtor.

I could stay afloat on both for a year. But realistically I would drop my asking price to get it off my plate. New house is a “forever” house, no stairs, 2400 square foot heated  shop with plumbing and 14 foot ceilings. There is also an airplane hangar, fully enclosed, I can rent out for $400 monthly.

Main 2 hurdles are having to move and convincing my wife that it is not crazy to do it this way.

I have always sold my home first before buying a second.  Just the way I'm wired.  Wanted no possibility of 2 mortgages at the same time for any appreciable timeframe.

My dad did something similar. His for sale house sat vacant for like 10 months. Wasn’t a big deal for him financially but having to upkeep two yards and make sure nothing bad happened to the vacant house for sale really sucked since they were 30 minutes apart.

Generally a furnished house sells better than a vacant house.  People struggle with empty rooms and often think rooms are smaller than they actually are.  That said,  living in a listed house does suck for showings.

I'd usually just roll simultaneously.  List your house and house shop.  If you buy the new house first,  great. If your current house sells first,  great,  you could still negotiate extra possession until you can purchase.

Sell your house first.

Rent.

Let this bubble deflate/market roll over before you blow half a mil on a 340k house.

I've been here for a lot of years.  That same advice has been given the whole time.

Im not saving be careless. But at what point do you be optimistic, make some forward moves, stop buying silver, and eat the stock piled food in your basement?

I've done this in the past, but my reasoning and execution was different.  There wasn't a lot on the market and what was there was going quickly.  I wanted to make sure that I didn't have some period of time where my kids were essentially homeless.  A good mortgage person can give you solutions to minimize the hassle of switching and having different loans on different homes.  What we ended up doing was prepping our house to be on the market while we were looking.  As soon as we found the house and had an accepted offer, we put our current home on.  Luckily, everything went as planned.  I ended up with both homes for a couple weeks and was able to casually move everything over.

A house that isn't being lived can also signal that someone else has moved on and needs to sell.  So, be careful how not lived in it looks.  You really just want it clean and with good furnishings.

The downside is that it will cost you loan origination fees which are probably $2,500 or more.  If you could buy the new house with minimal down, some loans are as little as 3%, then you could wait until you sell, dump the cash into the new place and have them recalculate the amortization schedule.  Assuming you do something like that it is just one new loan.

Find out how long properties like yours, or at least properties in that general area, are sitting on the market and plan accordingly.  One thing is that interest rates are moving around.  The 10 year, which is what loans are generally based off of, is currently moving down, but the fed has been increasing rates regularly.  If the rates start moving higher, you are going to end up on the lower end, and any property you buy could be a little cheaper.  If they continue downward it may help you on your current house and not so much on your purchase since you are essentially a cash buyer.

One question I would have, why the move?  With the price ranges you referenced, that would largely be lateral I would think.  It will cost you 6% on your sale in realtor fees plus all of the moving and loan costs.  If there is something you want out of your house could you not dump the $30k that you are going to lose into it and save yourself the headache?

I forgot to mention that if your existing home sits empty for any period of time longer than 30 days, you will need to get a vacant dwelling policy instead of your regular homeowners policy.  It isn't uncommon for them to be 2x as expensive as your current policy and they generally have the first 3 months as being earning premium so you wouldn't get that back if you sold inside of that timeframe.  Some people don't pay attention to this, but I promise you that if your house burns down or gets robbed 60 days after you buy another house and move then you will be staring a denied claim in the face.  You are better off doing it as soon as you move to start the clock on the minimum earned premium.

As someone who has made a living doing Real Estate, i’d do what you are thinking.

I’ll either rent or live with friends/relatives while i fix my empty place up and have it marketed.