Spending $15,000 on minor updates in a Hyde Park two-flat could raise the rental unit's value by $300/month.5.

The main issue is that to do the ADU you have to spend so much bringing other items up to code like electrical, plumbing, lighting (windows) and egress.

If you're earning primarily W-2 wages, interest, or dividends, those attractive depreciation deductions from your cost segregation study will be suspended.Think about it this way: You might spend $10,000-$15,000 on a cost segregation study, expecting immediate tax savings, only to find those deductions suspended indefinitely.Does this mean cost segregation studies are worthless?

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

A lot of people spend their time doing this, but it's not a good use of time because it can not teach you anything relevant without seeing each one in person.

If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.

Based on the questions you are asking I think you need to spend more time listening to podcasts like Bigger Pockets and Bigger Pockets Rookie.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

I'd look for a good brand and spend some time looking at reviews from a big box store. 

You can spend your time in worse ways, like watching some silly movie.