You know, I was thinking this exact thing myself. The game's economy is frankly pretty crap, especially considering how hard it is to actually make money. The upgrades, as you point out, are mostly worthless unless you're going to be playing for months and months, and there simply isn't enough content (or things to buy) for that to be worth it. They're just expensive for the sake of being expensive, making them borderline gameplay padding. It's probably the game's biggest flaw.
I Guess I am Not understanding what you mean,... I had No problem with it.
1) I bought Farm & 1st upgrade; (later upgraded Day Care)
2)Bought Bar, then 1st Upgrade (Advertising)
Giving me $600 per week, Plus Bar wages
(I had over $3500 before I Bought Manor & 1st upgrade (East Wing); (losing $100 income).
Currently, I have a lil over $2100 w/ $500 a wk income, Plus Bar wages (working Evenings*)
NOT going to bother with "Club" or Dungeon upgrade for now (No $$$ Upside)
Although, with CLUB Upgrade There should Have been; at least in Bar wages (from +$20 to +$50)
(Hell, I am The BOSS Right?? Give Myself a Raise.) LOL!!
Now, it is just a matter of waiting & saving until Updated story line to buy College.