Getting a house that has a back unit mother in law suite or apartment dwelling in the back and rent that part out to someone. 

@Deb L.There are many rules when it comes to writing off / capitalizing items such as improvements or repairs.Improvements may need to be capitalized unless there is an election in place that will allow you to write off the full amount in the first year.Alternatively, if there is something placed into service in the past and the item is no longer of value, you may be able to potentially write off whatever wasn't depreciated up-to that point.In general, it may be best suited to talk to a CPA to better understand your situation and give you more suited advice.

Single family homes with separate entrance mother-in law suites or garage apartments with full bathrooms & kitchens may be more appeasing to you and your parents.

The higher deposit and flexible closing date to suit the seller are also good.

Yes, that version is well suited to kitchen/ bathroom floors, particularly when it’s tile/ etc.  

I am not 100% sure of the exact details but our attorney helped us file suit but the effort was more about getting him out then it was getting him in trouble.  

Or better yet, work with someone who has the time to sift through all sorts of deals and show them to you and figure out what will suite you best!

@John R BehrnsIf the property was not in livable condition for 2018 / 2019 tax year, you should not have reported them onto your return(contract to an above poster).Those costs get capitalized and would be reported in the year that the property is rent ready.You have a good amount of questions and it may be best suited to work with a professional to help you with your filing.

However, when the mom took Tenant Y's phone and messaged me off that threatening to call the police and filing a suit for not allowing them to live for free, things got harder to say the least.

@Alejandro RomeroMy opinion on best approach for house hacking in expensive market like SD (which I am currently shopping around for as strategy as well) is a 4+ bedroom SFH with in-law suite or separate entrance for privacy reasons (3 bedrooms on one side of the house with own kitchen and then your own bedroom/ kitchen/ bathroom in your segment of house).