I was thinking I would reinvest some of the rental income to make some minor repairs/maintenance around the home.

In New York, you typically need to show an annual income of 80 times the monthly rent to qualify for an apartment.  

Until then, Id really like to set up some passive income in the city based upon buying and holding units for rent. 

Digital nomads, corporate travelers, construction workers, relocations, families experiencing an insurance claim and many, many more types of travelers are looking for furnished accommodations and they each have different requirements for what they're looking for.

When dealing with two separate houses on the same lot being sold together, it is important to consider several factors in determining how to calculate potential rental income.

Typical rates are 8-12% of income either monthly or yearly depending on manager.

If you are selling your business, what are you two doing for income now (goes toward financing ability)? 

I have W-2 income and three investment properties.  

Are you able to take advantage of the ADU as an expense against other income (W2 other gains) where you could get back most of it? 

@Erika Caba I think if at the end of the year when you can evaluate the situation as a whole with everything taken into consideration and are looking at your tax returns if your goals have been accomplished with this building, whether it’s positive cash flow, off setting W-2 income, whatever, then I’d say it’s too early to throw in the towel.