Hopsie, I'll throw in my thoughts for what they are worth (and I will add the disclaimer that I've been single for thirteen years so I'm not a relationship expert!). But.............
The way you are looking at this - both practically and emotionally, acknowledging potential problems whilst recognising what is good - is pretty amazing. It's so easy to fall into the 'my knight in shining armour has arrived' that I think the cool, yet kind, head you are keeping is fantastic so well done on that (I'm glad you've got your T to talk things through with as well).
I think him being open about the fact he's still dating is a good thing. He could easily have lied and likely you'd not have known any different any time soon so I think the fact he is honest with you (even when he's telling you something you might not want to hear) is good, in my opinion. Personally I think 'shopping' for a partner is what we all do and I don't think a businesslike approach to it is necessarily a bad thing. I remember someone I used to be friends with who was going through the arranged marriage process (Indian family). At first I was horrified that this smart, confident, well qualified woman was part of this process, but she explained to me that, because marriage is the aim, everyone is very open and matter of fact about it. Initial contact is a phone call where they discuss main expectations - do you want children, how many? Will the woman work or stay at home? Will they live in their own house or with family? What are your political views? How do you feel about x, y and z. And then based on that, they'd decide whether or not to meet and things would go from there. How much time and heartache does that save? Clear, concise, open conversations about really important things that often become reasons couples divorce. I think that's a good thing. So if he is 'shopping' for a bride, I think that shows he knows what he wants and he doesn't want to waste time waiting for it to come (sign of good self esteem, perhaps?) and to be fair, I think that's what we all do, it's just that most people aren't so upfront about it

I see no reason for you not to be dating as well, if you want to. I think the fact that he didn't react negatively to you saying you were still open to dating is good; he's not got a double standard where he thinks it's okay for him but not for you.
I think the fact you can talk for two hours over lunch is a good sign and yes, you are right, lots of conversations and q and a sessions aren't wasted time, and neither is just enjoying time together and hanging out in different environments. I think the most important thing is to enjoy what you do together without the end point becoming the sole focus? Which I know is easier said than done

I think his transparency about his negative traits is a good thing. He's aware that he has faults and is open to talking about them and acknowledging where he went wrong. It could be that this is only the tip of the fault iceberg - that's true of anyone - but spending time together, as you say, is the only way to find out. So far is he mostly telling you about his faults rather than doing them around you? I think him telling you about things he's not great with (rather than just showing you by telling you what to do) is a good sign. None of us are perfect and recognising that in ourselves is a good thing.
He may need a meticulous partner and a great cook, Hopsie, but what struck me about that was, what do you need? You are not a wall flower waiting to be asked to dance

You are an enormously kind, compassionate, intelligent, emotionally accomplished woman who has so much to offer. You've overcome some terribly traumatic events in your life without becoming bitter and resentful (a huge achievement, in my opinion). You've very practically organised your limited finances without doing the damsel in distress thing and just marrying some bloke for his money. You reinvented yourself repeatedly after losing your job in order to keep working and keep looking after yourself - smart, practical, diligent, wise. It would be enormously fortunate for him if he happens to have enough qualities that you desire for you to consider him at all! I think that's the red flag for me, that you aren't focusing on how wonderful you are and how lucky he would be to have you by his side (and I mean that in a kind way, not as a criticism

).
I don't think backing off slightly - to give yourself time to think and process how you feel, and work out which way round things are at the moment - is a bad thing. And, yes, that possibility of getting hurt is tough to handle, I think because there's no way around it? If we want to have other people in our lives we run that risk of being hurt. Sometimes we can handle it, sometimes it's too much. I know for me it's a barrier so I get that completely. But personally I think that you need to make an ' I Am Bloody Marvelous' wall in your home and write up on big pieces of paper all the amazing things about you, Hops. You have so many good qualities and you've overcome so much, you blow me away and I truly mean that. I get the not wanting to get hurt or to find yourself trapped in another unpleasant situation but I think maybe spend the next bit of time really getting into your own mind that he would be really lucky to have you and if he has half a brain he won't let something like having to cook his own dinner get in the way of that. Maybe take stock, put those reminders on the wall (I'm serious about that, I think you need to have things printed up in giant capital letters so you can't not notice!) but also have a good think about what you want in a man and how many of your boxes he ticks? He may well be sitting at home now wondering if he's matching up to your expectations

I think it's amazing that you're going about this is such an open and honest way; it's very refreshing and brave of you to dip your toe in the water again (I know blokes make all my 'what ifs' bubble up and it's hard). But I think you're going great guns and I hope the next date is a fun filled one that maybe takes the wobble off everything a bit
Love Tup xx xx xx