A red flag or just anxiety?

I lost my husband 7 years ago and needless to say, it was and continues to be traumatic. He was my best friend, spouse and all of the rest. We built a beautiful life over almost 30 years with 2 beautiful children. I dated many people after the first year or so, but somehow it never feels right all of the time. By this I mean that I could enjoy myself for dinner and even a short trip with my partner but afterwards I'll always feel empty and anxious about moving forward in the future (long term, like rest of my life) despite how I cared for the person. One in particular has been someone I've known for many years and we have dated but I have broken up with him a few times after I realized that while he is very loving and we have a great time together, I don't think he is the "most compatible" one for the future due to our financial differences (i.e., he will need to work much longer than me and has very limited funds vs. I can retire soon and be comfortable with the earnings and savings I have made all my life along with some money my late husband left me). So my question is: I do love the man I've been dating for the last several years despite our breakups and we always reconcile after a short break. The last time I was determined to make it work. Now that we've been together for the last few months; the beginning was wonderful (I really missed him and vice versa) and I needed that love in my life so badly. But, I'm really worried that our financial differences may come back to haunt me. For example, my family who I don't see any more than once a year due to distance, invited me, my son and my bf for Thanksgiving out of town and both me and my son don't have work that day or the next day but because my bf has to work the day after Thanksgiving (and the following day as well), he said we should stay in town and go to his daughter's house. I asked him if he can take off at least that Friday and he said it will be a busy day (he works retail). Frankly, I'm disappointed because I don't know when I'll see my family again and I have a large family. I realize we need to make sacrifices for our relationships to work but is this reasonable to expect me and my son to miss our family holiday? Another example is travel. He is very limited in terms of time off of work and how much he can spend (we split the cost) so any travel is limited to a night or two every now and then and usually only because we are invited to an event of his friends or family. I used to travel with my late husband and that was my (and his) great joy in life (besides our kids). We took off 10 days every year and went to Europe, etc. Our travel was cut short by his illness and we never got to the places we wanted to (and I still do). As a matter of further background, I am 61 and my bf is 66. Am I seeing "reality" now and if so, what is the right thing to do (for me)? I am sick of searching for the "right" one on the dating sites, etc. No one makes me feel as loved as my current bf. Your advice is appreciated.