Or were you mainly referring to if it were two separate parcels - which I’m guessing was your angle?

My opinion- You should not get into Residential Assisted Living because it fits your work from home lifestyle. 

Most investors began with nothing but curiosity and a desire to change their financial future.Focus on education, networking and understanding the strategies that fit your current situation.

When I buy my primary home it has to fit my PERSONAL needs.

.• Down payment assistance programsCalifornia has several, CalHFA, GSFA Platinum, and county-specific grants.You don’t need all of these, just the one that fits your situation best.3.

There is not going to be a one sized fits all ROI for these upgrades.

From a tax angle, that two-family is a solid start because you can use depreciation to reduce taxable rental income, and your cosmetic upgrades may qualify for deductions or depreciation (like someone above mentioned, definitely look into cost segregation), depending on the work.

If you're not able to find the right fit, I would recommend either finding a value-add rehab property or just a long-term hold rental.

There's no perfect fit but if you schedule time in your calendar as opposed to reminders, that could work.

Also, some that I have come across are really not numbers-oriented people like me, and I am getting the impression that that isn’t too uncommon.I’d like your take on something if you are open to helping me understand it: why do I see many RE folks approaching deals from only one angle (i.e. cash flow or appreciation or amortization or value add or tax appreciation) rather than aggregating all 5 categories together into an accurate model to sum up the financial gain of a RE investment.