Replacing what you earn/your lifestyle will take more time and effortFor me it was easy to replace minimum wage with rental income and flipping   My sister on the other hand, making probably around how much you make, proved impossible for her and she had to wait to retire until she was in her 60s    I, on the other hand was able to retire in my 40s because of a more modest lifestyle for you and most people the rental route is a long route.  

I just spent $2k replacing 2 garage doors.

I'm not replacing window but did repair the foundation.  

They have bills to pay on the property like taxes, insurance, mortgage, utilities, maintenance and repairs, and replacing components of the home (cap ex).

Thanks Michael, There is definitely a lot of work to be done:- Paint is pealing off all the walls- New appliances for 3/4 units- All units are required by the TWP to be connected to sewer now- Bathroom rehab for 3/4 units- Above ground oil takes removed and boilers replaced or retrofitted for NG (This is more a nice to have)I asked the owner if he would be willing to do owner financing and he said no...

Because of the restrictions for cars, you may be better off from a tax timing perspective if you replace your business car with a heavy sport utility vehicle (SUV) instead of another car.

Not like you have to replace the whole HWT. 

If you looking for additional income, to replace a job, etc, cash flow is likely what your looking for.

EVerything else, as long as you have positive CR is paid for by the tenants, and spread out over time in very small increments.Now this is a commercial property, but I will give you an example of a SFR one where the roof will need to be replaced within the next 5 years, and I will have the original financing pay for it now, and why. 

Worst case the wall needs rebuilt and joists replaced.