If you need more space, less space, better space, or a different location, the biggest conundrum is to either buy or sell first. Both scenarios have their tricks. If you buy first, the risk is not being able to sell your home in a timely matter or the sale price is not what you anticipated leaving you with two properties and the resulting costs. You could end up with less equity or both.
Conversely, if you sell your home first and then can’t find a suitable home before your sale date it’s a big dilemma. In many cases the bank won't lend you enough money to buy a second home, so question answered.
In these situations I recommend getting a good real estate professional who is willing to work with you until you are sufficiently comfortable with the prospects.
First, do the homework to see what types of homes are available. You may need to see quite a few homes that work for you and then hope they stay on the market until you’re able to buy. By doing this you will be able to get some comfort that the type of home you are looking for will come available when it’s time to by. Secondly, be honest about the value of your home.
If it’s on the market and not selling, it’s likely overpriced. There is three things that effect saleability. Location, condition, and price. You can do something about condition and price. In unique cases, your home may require a particular buyer and time is an additional ingredient that is required.