I even sanded the floors myself and it's the last time ill ever do that lol.It was quite stressful living through the flip, but when I finally got it sold with no capital gains (lived in it for 2 out of the last 5 years). 

The realized gain on the sale will be $430,000 - $165,000 = $265,000.

When the owner of the asset is also the owner of the crypto company, I think the transaction can't be used as a valid example of the technique gaining traction.

My recommendations would allow for a full step up on basis upon your death; important if you have a built in unrealized gain on the residence. 

I personally gain valueable info and make connections each time I have attended. 

Bought my home Dec31 2020 in Van Nuys, CA (Los Angeles) for $586k. (5% down, 2.99%)Seeing very similar homes in my neighborhood (with even worse specs/curb appeal) going for high $800+ as of 2021.Not ready to move on yet, but just trying to plan ahead, as I'm considering relocating outside of LA in the next few years, and will need to capture some of that appreciation gain to make a healthy downpayment on the next home.

Between the original closing costs, foundation repair, pipe repairs and water damage as well as the taxes and commission to sell it you still could come out even (or ahead), however, if you've fixed most of the issues at this point you might consider waiting to gain more appreciation on the property before selling.Reading your second to the last sentence it's written in a way where you may have already made up your mind.Good luck,-Chris

Congrats on taking the next step in your investing career--it sounds like you already have a solid footing with the experience you've gained from the 4-family.I'm an investor and investor-agent based in Northern NJ, so always happy to connect and expand the network.

How can I gain confidence in this?

If it makes sense get it and gain some experience.There is no time frame.