CoffeeBuzz: Observations on almost everything

I've been in relationship with J for a little over three years. I'm nearly 53, and he's 56. Both divorced -- him twice, me once. Neither of us have ever had kids, our parents are gone, and we have no living siblings. We actually met some 20 years ago in Ohio as colleagues in a volunteer organization, then lost touch for many years. He looked me up on Facebook about 4 years ago, when I was still living in Ohio. I was already planning to move to Maryland at some point -- it just seemed like a pleasant place -- and he happened to be living in Annapolis. As we rekindled and developed a closer friendship, he offered to help me move here to Annapolis and give me a place to stay with him and his (female) housemate in their large rental townhouse while I got my feet under me. During the several months of prep time it took me to arrange to move, including finishing a contract position I was working in, things began to move in a romantic direction between us. On the day I arrived in mid-April of 2014, he offered me the option of my own room which he’d already furnished for me, or sharing his room as his live-in girlfriend. As we'd already become romantically and sexually involved, I opted to share his room. He told me he loved me and that he was thrilled by the direction things were taking between us.

I made it clear up-front that if we were going to be serious, I would eventually want us to marry. Although he was leery of marrying again, he said that for me he would actually be willing to consider it as long as we took financial precautions. (His second wife took advantage of him financially in their divorce.) I told him that was absolutely fine with me. Let’s face it, prenuptial agreements make a lot of sense in this day and age.

At the time, J had a job he absolutely loved doing sales and marketing for a well-known consumer goods company, was nearly debt-free, and earned about $100k annually. He worked from home 90% of the time and had great benefits, a company car, and all kinds of perks. He was very happy and quite proud of what he'd accomplished for himself in his career, especially given that he'd had some rocky years in times past. By contrast, my savings were depleted, and I had nothing except my skill-set, determination, and a fierce desire to carve out a new and more satisfying life in new surroundings. My career is in office administration, project coordination and customer service, and one of the reasons I'd chosen to leave Cleveland was due to the extreme shortage of good-paying jobs in my field. I'd been stuck earning about ~$30k -- and sometimes less -- since 1999, not counting the four years I'd taken off work at one point to care for my elderly father who suffered from dementia and other issues. I was truly attempting to start over, and J knew that and wanted to help.

All of this long, drawn-out, probably TL;DR thing is by way of saying, if you’ve read all the way to this point: What’s your take on all this?