We need a larger home for our family, that would be functional for multi-generational living with our kids and our parents living with us.

In real estate, this means buying properties that generate income—while we sleep—and (ideally) appreciate in value over time.

Market cycles and long-term perspectives will continue, but local investors can build generational wealth by adapting strategies, being patient, leveraging smart financing, and focusing on long-term wealth-building.

How much do you need to generate in investment income to either step away from your current job or do something you enjoy more but less pay?

But the question is whether one can actually achieve the proforma cash flow on older properties with a less economically stable tenant base.Based on your picture, you appears fairly young.My advice is buy properties in quality locations think long term 10 to 15 years - slowly and safely build your portfolio - equity and cash flow will increase over time and in 10 to 15 years you may become financially free.People talk cash flow is king but one can NOT generate financial freedom cash flow with $250,000 or $500,000 invested (equity).Even at a 10% cash on cash return, one needs $1.2M invested to generate $120K a year $10K a month.You want property to be self supporting so it needs to cash flow but once that is reached the focus in my opinion should equity growth which increases net worth.

During this time you are not generating any return from the money invested in the ADU.

Mostly just looking generate better cash flow than I can here in Madison.

If I rent out my current primary residence, I could generate over $1K in positive cash flow, so I'm considering moving into the rental property and handling the repairs at a more manageable pace.

An active wholesaler and houseflipper in my market says that newer investors should expect to spend nearly $5,000 on 1,000 mailers for 6 months just to generate 1 quality lead (citing a .1% conversion rate).

The 20% down payment isn’t a concern for me; my primary focus is ensuring the investment generates positive cash flow, which is what my post was aimed it.