And now he lives in a lovely $1.2M home in Waltham, MA with three kids and a wife and retirement savings + equity in the home totaling $600K against maybe $700K in debt on his overpriced house and multiple late-model cars.

I am a retired HERS rater and now builder of multi million dollar commercial buildings.

Just retired this last school year from my teaching job and only work on the RE business a few hours a day!!

Purchase price: $264,000 Cash invested: $53,000 Sale price: $385,000 Bought great 4 family in fitchburg at a great price from a retiring landlord looking to edit the game.

While an SDIRA can be a great way to increase flexibility and get higher returns with retirement money, it is not a direct substitute for your own investing.

Hard money wont finance if you live there they like like to avoid the dodd frank laws and primary occupancy consumer protections most likely so you'll be left with heloc options to tap equity, 401k loans from your retirement, savings/cash, and cash advances to fund your rehab. 

My goal was to create generational wealth for my family and have solid income during retirement.  

Buy the property with an FHA loan (since I don’t have a ton of cash, most is invested or in retirement accounts.) and then move out after the requested timeframe has lapsed that I need to live in the property.My current lease I signed was an 18 month lease and we have still around 16 more months to go.

Even if you are fully retired, it probably wouldn't be a bad thing to participate a little bit to keep your mind moving.If I were in your position, I would be focusing more on cash flow rather than appreciation.

I've bought two off market deals thus far but we paid an agent (basically retired) $400 to push paperwork at the closing.