So, after playing the game extensively, i can put down quite a few notes for anyone playing the game.
The earliest you can get the good pregnancy ending is 150 trust,and must have 50k money on hand. Anything less than that and you'll be forced into the bad ending. I also recommend around 100 sexual interest for the imouto, so you don't get hit with a big mood drop after doing the deed with her. After reaching the good pregnancy ending, your job title will be forced to change into a office worker, no matter what it was beforehand.(Gotta pay the bills and support your imouto and the baby after all!)
150 trust is also when the imouto will start accepting offers to bathe together. You need to have her at good mood or higher. Hitting this goal is important because it shortens the time spent on baths, and you get +2 trust and +2 sexual interest everytime you bathe together with her. 200 Trust is when you can really start grinding the imouto(snicker) stats, since chatting with her in the bath can rapidly raise stats, especially paired up with lots of gaming with her.
Try to buy the gal game (7000 yen) and the lewd game (12000 yen) from the game shop (or shopping online during the weekday) ASAP. These two gaming options with your imouto is one of the fastest and reliable way to increase trust/lewdness during the weekdays.
Depending on the type of onii-chan that you roll will affect your gameplay. You can sort of influence what type you'll get with certain choices, and certain adjectives will affect your max energy between -10 to +10. Also your starting max vigor can be affected anywhere from -1 to +4 as well.
Office worker will start with 30 base energy, and will get a income of 40k every sunday. Weekdays you'll be forced to work until 19:00 hours, and some extra time travelling,it's recommended you spam bento boxes during the weekday so you can save a little extra time to get at least 1 bath and 1 gaming time with the imouto to raise trust levels. Time is your biggest enemy here.
Student will start off with 60 base energy, but has only the allotted 15k per sunday via allowance from parents. You can earn a extra 5k on sat working part time, and another extra 5k on sunday,also working part time. Money will probably be your biggest gate here.
Part-timer will start off with 40 energy, and will get 25k every sunday. You get 1 free action before being forced to go to part time everyday until 18:00 hours. Sort of the middle ground here.
The bum is the "hard" mode, and is probably the toughest one to do anything with. Starting off with 25 base energy, and only getting a allowance of 15k per sunday. For the love of god, if you roll anything less than 25 max energy, RESTART. It becomes WAY too hard to do ANYTHING if you don't have at least 15 energy to take walks around the neighborhood to even start raising your max energy. You probably also need to get enough max energy to start working part time on sat/sunday, because every single yen counts. Having ver 1.3 with the compensation rewards for all the previous version bugs (20k x 2) will REALLY speed things up, especially if you get lucky enough to do online shopping during the weekday, and getting access to the dumbells for a quick +5 max energy.
For part-timer and the bum, during the weekdays, taking a walk around the neighborhood THREE times will raise your max energy by +1. If you have the "Buff" (Or was it "strong"? Not sure which one.) title associated, it only requires TWO times to raise max energy by +1. On the weekend,however, if you workout with your imouto, you get +1 energy everytime.