Engagement ring - no way. If she loves you and you don't have the money, she does not NEED a ring, a ring is just a symbol of status, nothing else.
Sheslinger, I would have agreed with you in the days before I became religious. However, part of what is required in Orthodox Judaism to officially become engaged is the giving of a valuable gift, and it has come to be that a ring is now what is expected. There isn't much choice there. Maybe I could get away with a cheaper ring or a diamond bracelet, but I need to give something along those lines (and if I have to give something valuable, then for my emotional satisfaction, it must be a ring of at least middle quality). The only other option, and I'm sure knowing most women I'd be taking my life into my hands if I suggested it, is using a car as the valuable gift and "kill two birds with one stone", then maybe buy the ring later. Actually, a bit more realistic might be buying the house a little sooner and using that as the valuable gift, I might survive that one (women, with exceptions, aren't usually into cars, but many are into houses, and both seem true with the woman I'm dating).
You are trying to do an awful lot in a short period of time. The whole thing sounds like sort of an impluse decision where you decided this is what you want to do and it has to happen yesterday. Take your time, do what is in your best interest and you will live happily ever after.
I know it may seem that way, but it is not as quick as it might seem.
-House: I am 34 years old, I've been thinking about it for years. I also used to work in the financial field (sort of, it was retail/consumer level banking) so I know that renting is a waste of money and I don't want to do it again if I don't have to. I can live with my parents for some time right now so I will do that and save for a downpayment (mortgage payments will probably be less in the houses I'm considering than rent would be). The only thing fast is that I'm old enough that I'm not waiting years (a year plus or minus a few months or until I'm married, whichever comes first) living with my parents, and I just got a good job 2 months ago.
As others have said, you don't always need 10-20% for a downpayment. With decent credit $0 will get you a house with expensive mortgage insurance. FHA loans or good negotiation skills can allow a smaller downpayment without mortgage insurance. Also, potentially keeping down the downpayment, where the Orthodox community is in Baltimore I can get an acceptable house for $160K or a nice duplex for $100K, though there are some pretty expensive houses too.
-Engagement ring: I am an Orthodox Jew. I should have been married years ago, but I only just now got a good enough job to consider it. We don't date long. We date with an eye very seriously set on marriage, we ask the big questions early, and so we tend to know fairly soon (and with "chemistry", to a degree it is there or it isn't, it isn't usually developed). Also, once we know who we want to spend our lives with, we aren't waiting because in our religion we can't so much as shake hands with someone of the opposite sex we aren't related to. Can you imagine the emotional stress of being in love with someone and not being able to touch in any way, not even hugs or hand holding? As a result we usually are engaged or broken up within a couple months of meeting (often
much sooner), and married within a few short months of the engagement. It works, I haven't always been Orthodox but I have been for several years, so I've seen plenty of married couples both Orthodox and not and most of the happiest, strongest and longest lasting marriages I've seen are Orthodox Jews.
-Car: I just bought a new car when I got the job, good thing too since my old one died a month later. I want the woman I'm dating to get a new car because her's is a death-trap. I wish she already had a safe car, but she doesn't. Not much I could do about that. If we marry she will need a new car asap (I won't have my wife, when/if that happens, driving an unsafe car). The only other option is if we can get by only with my car, and I'm not sure that is a possibility (not in the beginning when I'll be working 40 miles away and she'll probably be working too).