After quitting I would want to be doing real estate deals more full time and do something more enjoyable to supplement my real estate income (maybe teaching or personal training- tbd).I’ve thought of buying 1-3 more properties within the next few years and then using the income from all my properties and job to hammer down the mortgages.

@Edward Schenkel Great advice above - What are your thoughts on supplementing with an umbrella policy? 

You can supplement the funds that you're taking out of your home through additional funds from hard money. 

Life insurance has no minimum distributions like retirement accounts, but can be used to supplement your retirement if you’d like. 

ROI - I don't mind your use of AI, just use it as a supplemental tool to your other tools.

I'm ex-military so I have VA health care and purchase supplemental for my wife. 

I have long wanted to hold rental properties as retirement assets and to supplement my income from my full time job.

I have long wanted to hold rental properties as retirement assets and to supplement my income from my full time job.

I see all these younger investors when you ask how much do you need and your done.. and many will answer 7 to 10k a month.. but as you age out health insurance ( if you want the best like we do) is going to take a huge bite out of that.our medicare and supplemental is right at 2k a month for both of us total so If we though we could live on 10k well thats really 8K..

Income Potential: Rental income from real estate can provide a steady stream of passive income, which can be particularly attractive for retirement planning or supplementing other income sources.While your family member raised valid concerns about the risks and expenses associated with real estate investing, it's important to weigh these against the potential benefits and your own investment goals.