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Being a rural dweller by choice, neither one appeals to me much, although, #1 would be semi-acceptable, #2 is, well, "Number 2" as a small kid might put it.
How do I hate HOAs? I need a serious computer to count the ways.
The only thing about #1 is I would want a garage, if at all possible.
The other point is I would (in your region) want a seriously uprated heating system and insulation in the old house - but of course this is stuff you can do after the fact if it's not there when you buy it, the thing would be not to pay too much for the house and to not over-upgrade it.
#1. The commute time and the un-walkability of the second make it a deal breaker for me. That extra 40 minutes you spend stuck in traffic everyday? You never ever get that time back. Ever.
A ten-minute commute also means you may be able to swing lunch-at-home, which is both a huge luxury and potential money-saver.
Finally neighborhoods change ove time, both for the better and the worse. #1 could possibly gentrify and one could see the value of the house/lot rise. Sad to say but many houses in outer-ring suburbs such as #2 have no where to go but down.
I'd go for the door number #1. I live in a similar neighborhood except there are not so many children here.You can walk to some businesses which is a good thing. You'd save money on gas for the car.
If you really don't like either of your choices then just wait a while. More houses will come up for sale.
I couldn't deal with the zoning gestapo telling ME that I can't have a clothesline, or colorful patio lights. And I hate those ugly white mercury vapor lights in subdivisions. They are hideous. Sadly, they are showing up all over the place. Nothing runs a town into the ground like ugly lighting ! I want a house like the Addams Family.
#1. The roomy bedrooms! The wire fences seem unattractive to me so I'd put up my own. The commute, and the proximity to shops is really good. I don't like McMansions they are homes with no character.
I'm not a fan of either scenario, however I chose #2 because the list of issues pertaining to #1 would make living there unpleasant. I don't want to hear other people blaring music at all hours. People selling cars in the neighborhood? Junker being worked on in the street? Why not the garage? Next door neighbor has frequent parties on the front porch?
It doesn't matter how much more charm an older neighborhood supposedly has when compared to an HOA; a neighborhood as good as its people. And if you've got noisy and annoying neighbors, that charm will wear off really fast.
#2. The first one has too many downs: built before my grandparents were born, wire fence (I like my privacy when I'm in the backyard, I'll take a dark stained, overlapping, metal post, eight foot wood fence), cars on the narrow street, parties (yuck, I've had fifteen years of putting up with this crap living in apartments!!), kids in street...
#2 seems like a caricature of modern houses/neighborhoods around here, at least for me. For example, the ultra-short commute, for me, is to be found in the brand spanking new houses. Mine is eight minutes on a good day. Since I'm single the bedrooms are unimportant to me, want a large central place. Two models and two colors -- seems like an exaggeration. Is it more like ten models and thirty different brick and stone combos plus differences in front porch, garage etc.? In my case my beloved park is a short bike ride away, although I probably won't be riding or walking to restaurants or shopping centers. And the HOA ($150/year) is so far very reasonable.
#2 by a lot, but you can alleviate a lot of those problems.
I'd keep looking, but I suppose if I had to make a choice it would be #1.
Sounds like some of the problems you mention could be solved with a few well placed anonymous calls, maybe there are city ordinances about the street parking, running a business in a residential zone, loud noise, etc.
The chain link fencing would be a big "ick" factor, but I suppose in your own yard you could hide it behind a plank fence or some shrubbery.
#2 sounds sterile, boring, and too much under the control of somebody else. If I had to ask permission to put a garden bed on my own property I'd cry, or curse, or something.
Neither sounds appealing so I didn't vote.
#2 sounds like a really strict set of HOA rules, most are not that extreme but I'm sure there are such places.
#1's charm and character is going to wear off fast when you ask your neighbor nicely to turn down his music and he tells you he can do what he pleases and you can shove it up your ***.
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