The Sims 4 Three Little Sims Challenge

Well, it's official. Since I deleted my first attempt at this Challenge, I'm starting over. Keeping the same crew, since I like them. We have Xavier (my painter), Yousuke (my writer) and Zach (my techie guy).

Picture this: Three fellows, moving into the same townhouse condo development on the same day. They introduced themselves to one another in the Common Area as each was lugging his belongings into his unit. The units are attached but have separate entryways. Friendships sprang up immediately as each recognized that the others had wicked senses of humor, and they spent a good portion of the afternoon joking around. It was as if they'd known each other all their lives.

As the day wore down, they decided to share a meal before heading off to their individual units. That Xavier in the long-sleeved shirt, Yousuke in the black tee and Zack with the scarf:


And here is the development. As you can see, it's sort of a fixer-upper. Doesn't even have siding and the lighting is abysmal. Poor guys can barely see inside when it gets dark out!

It doesn't look as dark in the picture as it does in-game because I took the photo in the afternoon AND I brightened it significantly (photoediting) before posting it.
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Three questions and one observation:

Question: Given how much money flows in and out (painting expense, painting income, salary and wages, food expenses, it is really difficult to keep all the finances separate. Is this essential to the Challenge to keep the finances separate?

Question: One of the scoring components is to meet a Lifetime Aspiration. That sounds Sims 3-ish, since you couldn't easily change Lifetime Wish. However, since we can swap Aspirations anytime in Sims 4, do we need to keep the same Aspiration for the whole Challenge? Is the Challenge over when all 3 have completed their first (and only) Aspiration?

Question: Unlike Sims 3, there is no way in Sims 4 to determine number of paintings or books created. Are there other SIms 4 type things you'd like for us to achieve to satisfy this particular Challenge?

Observation: Make sure not to spend all your start-up money when first starting the Challenge. I'd say, leave a bank of 2-300 to cover incidentals. I spent all the way down to 19 and barely had enough for the guys to feed themselves that first night. Poor Xavier couldn't even paint because it costs 50 to make the smallest painting. And, since I had neglected to buy a trashcan, they couldn't do dishes (because they hadn't cleaned their plates).

Having fun so far -- just completed Week 1, Day 2 :).