What would you advise if I were your client ?

This is a great question and honestly a situation I see quite a bit here in Treasure Island and throughout Florida. I notice you are in a different state and that is why I mention location. Because we are such a transient state, with people relocating in and out all the time, it is very common for a sale and purchase to be connected like this. The key is not just the price, it is making sure the timing is structured so everything lines up. The biggest thing I would be careful of is relying on the seller of the home you want to buy to find something without a clear plan. Since they are not on the market, they do not have any real pressure right now, so I always try to create some structure around that. Basically, making sure there is skin in the game. On your side, you are in a strong position with a cash buyer. That gives you flexibility, which is a great place to be. If I were guiding you through this, I would start by asking your buyer for a slightly extended closing, something like 45 to 60 days instead of a quick close. Most cash buyers are open to that, especially when it is explained that you are coordinating your next purchase and want a smooth transition. This is often a better solution than agreeing to a rent back that you are not comfortable paying for. If they are really set on a rent back, you can still negotiate that. You do not have to agree to cover it fully. You can offer a short period or a fair daily rate so it works for both sides. At the same time, I would not wait to get the home you want under contract. I would move forward with an offer now and structure it with either an extended closing or a contingency that gives the seller time to secure their next home. That way they are committed and actively working toward a solution instead of just thinking about it. The goal is to get both sides moving forward together with realistic timelines, rather than closing your sale and then waiting with no certainty. This is something I navigate often here in the Treasure Island market, and when it is handled this way it usually keeps everyone in a much stronger position and avoids unnecessary stress. Hope that helps.