That was always the plan. She wanted to get a popup camper but instead I suggested a bigger boat that we could stay on. She liked the idea better then staying at a camp ground. We don't need a lot on the boat to stay on. Still young enough that its not a bother to "rough" it. But I still would like more head room. Could I live with less for now. Yes
I would concur with others that you should go ahead and get a boat you are more comfortable on. However, even jumping from a $500 boat to a $5000 boat will not solve all of your problems. A $5000 Catalina 27 will probably still need plenty of upgrades, or equipment replaced to make it safe and comfortable. But at that price should be ready to sail as soon as you buy it. I also agree that you are not going to find many boats <27 feet that have standing head room. Keep in mind that it made a lot of difference to me going from crouching head room (Catalina 22) to just shy of standing head room (Bristol 27).