A nice guy but...

Hi all, I hope you all are doing okay. I have some concerns about a potential guy I'm speaking to who I am getting to know for marriage purposes. I'll be 29 in a couple of weeks and he has just turned 27 last month. He is a sweet guy but often got rejected for his career, has no degree, appearence etc. When we first spoke he was ranting about the past experiences he had and how deflated he seems. I tried comforting him and trying to think positive but he was guarded and offloaded a lot. Towards the end he calmed down and said he would catch me before i left. Later on i found him talking to my family and his sister was with him. We all got on really well, my family like him and his sister is so lovely. My mum has good vibes since she met him and said she never met a family so similar to us. Fast forward to now, i am a little overwhelmed with the attention i am getting. He already seems committed and ready to take on the next step. There's some things im starting to pick up on which is he seems to need a lot of reasurrance and fishes for compliments a lot. I also discovered that he hasnt kept a consistent job for longer than a year nor has he progressed into a higher field. I feel as though he is the type to get upset if I say I would like him to develop in his career and to get out of basic level work. I'm not sure what his financial situation is like and I know he want to stay living with his parents after marriage. Other than that, he has qualities of a caring, respectful, considerate person. I feel hesitate to ask deep questions because of what he says for example, he often tells me how much he likes me, how i made him forget all his bad experiences with girls, how he feels good about us etc. Any advice?