I 'gave-up' and started farming...

Play the game as you wish.
I purchased multiple houses early on in the game to get return on my investment faster and now I am in profit mode.
Don't buy houses now as I have enough but while I do have rows of houses they are spaced apart and all have roads.
I buy land now as part of beautifying my town, but I'm proud of my town as it looks nice - you can have multiple houses with a great looking Springfield.