In order to achieve your goal and be safe, your approach here will be based on the following:
1.) Discovering the true value for your home in order to determine what "cash on hand" you will be able to work with.
2.) Having proper verbiage within the sales contract in order to avoid being homeless when closing escrow.
3.) Performing due diligence on making sure the home your purchase is within the Kennedy H.S. district.
4.) Due to interest rates moving upward this week, it will be very important for you to determine your max target interest rate. So that in the event our loan market moves upward to a point you are no longer comfortable payment wise, you can re-evaluate your decision.
Since our inventory is very low right now, sellers seeking to sell have an advantage especially if you have any equity in your home.
As the others have mentioned....you are going to be tight with the sales price/equity to put into a new home. But something to remember is that everything in Real Estate is negotiable. When you are buying and selling....it's a bit of a puzzle to get all the pieces to fit, but if they don't fit....you don't move.
You have a very valuable asset to a buyer.....you have equity. You are not asking them to wait for 6 months for an answer. Buyers right now wait months for a short sale only to find they are then asked to pay off past due HOA fees or extra money to pay off a second trust deed....and they do it. Something we can do for you is to ask a buyer to pay your closing costs. I have 2 homes in escrow right now with equity sellers who are having all their closing costs paid for by the buyer.
As far as commission goes, if you are buying a new home.....then you can usually get a Realtor to rebate you some commission on the new purchase (I do) when they handle both of your transactions. We can try and bring in our own buyer for you....trickier, but with enough time...and you are in no rush.....that would also save commission costs for you.
Now....the homeless aspect...yikes, bad idea! One way I handle this with sellers is we list the home and accept offers subject to you finding a new home. It's backwards from what you might expect....but why not? Buyers will wait 4-6 monts for a short sale....we are asking them to wait a few weeks for you to find a new home....to buy or rent.
It's the puzzle....but if you'd like to take a bit more about it and get a better feel for my ideas, shoot me an email or give me a call and we can talk more.
To then purchase a place for $300k, you would usually need at least 3.5% down - $10,500., PLUS closing costs for your purchase, as well, which, with lender's fees amount to another $4-7,000., so probably a need for at least $15k, just to purchase the next property. ( Which appears to exceed the amount you'll be receiving from your present house's sale.)
To me, given the numbers you provided, I just find it rather difficult to successfully massage the numbers needed to accomplish your goals - the reason I suggested renting your place out, rather than selling it, and then renting a smaller place, in the Kennedy District.
It REALLY all depends on the true value of your present home. ( And the integrity, or at least accuracy, of the source you're using for that figure.) Good luck in getting it all to happen according to your wishes.
Here's another thought. Since we're pretty close to the bottom for your price range, why not keep your present house, and make it a rental? You can probably cover your payments by doing so.
What you WON'T be able to do is buy another house. ( Lenders won't lend to you on a new house, while you have no equity in your rental property.) Solution? Just rent a smaller house with a lower rental payment.
Your old house will eventually grow in value more than a smaller house - so, let the tenants make your payments, and sell it someday when the market gets better - which it always does.
Of course you could save all that trouble and just stay where you are. Have you tried to refinance to a lower payment?