There might be some added tax benefits for this if you add in depreciation to help push you to a lower tax bracket. 

Similar to the comments above on using FurnishedFinder, also check Airbnb and sort for 30+ day rental options. in addition, I'd recommend talking to the local university and hospitals nearby by calling to their various departments.

One of my early properties barely broke even, but after a couple of years, rent hikes and expense optimization turned it into a strong performer.For cash flow benchmarks, I usually aim for $200-$300 per unit, but your situation.. house hacking.. offers unique benefits like reduced living expenses and quicker equity buildup.

This initial negative equity position consumes the initial cash flow.  2) the addition of the adu makes the property multi family and likely makes rent control apply.  

By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!

Many insurance companies do not allow adding a landlord as additional insured.  

Make sure your real estate agent isn't just about closing that one deal but understands the benefit of protecting you on each purchase to ensure that you keep buying because you are enjoying success.  2.

Hey Tim, Under IRS Publication 523, as a military member on qualified extended duty, you benefit from an extension of the “2 out of 5 years” rule to “2 out of the last 10 years” for excluding capital gains on the sale of a primary residence.

Use the ge benefits that you have earned to their fullest. 

Jim your also describing one of the huge benefits of being a transactional RE Broker ..