Also, optimize the new assisted living facility that we just purchased in January.

. --- They will offer to fix them in exchange for lower rent, but ask yourself, if the tenant has been living there for 25 years, why isn't everything fixed already?

Selling to an entity you own and renting from yourself looks like a tax dodge to the IRS, and they’ll likely reject it.Better AlternativesIf you’re looking to maximize deductions, consider more straightforward strategies like:Renting out part of your home (like a basement or room) while still living there.Keeping clear records of home office expenses if you work from home.Investing in other rental properties that aren’t your primary residence.Michael Plaks explained it really well in his response.

We paid off our primary home last year and have been slowly getting the courage to jump into the investing market where we live in the Pacific Northwest.

Hey @Jerry Nogueras - I was in your shoes too, born in NYC, and lived between there and Long Island. 

Quality tenants aren’t going to live in D properties.

I moved to miami florida to study the economics and help apply it and it was a capital market as well. if you don't live in a capital market like Chicago, New York, Austin Texas, Los Angeles, San Francisco, california or miami florida I'd recommend moving to a market like that too. it will change your life. 

The property has to be considered 'in service' for you to list it on your tax return.In service entails a couple of items such as1) The property is in livable condition - Working bathroom, kitchen and an area to live.2) The property was advertised for rent.Best of luck

I know becoming a part time agent is one way, but where we live in south Florida seems to be overfilled with agents and I don't think its a great fit for us right now. 

I wanted a house for myself to live in and I had been living with parents for two years to save money.