I'm looking to network and build relationships with investors, and gain as much knowledge as possible.

The longer you reside in a home the harder it is for most people to turn into a rental because it gains emotional significance.  

I know we all get busy but spending the time and effort to gain that person's trust and build a great rapport is surely worth the time. 

That way you don’t have to deal with the day to day and maybe can gain some perspective and reduce your stress from the property.

It's not just the amount of the gain that needs to be reinvested.

I’m concerned about capital gains and how this could possibly be a problem in the future.

It is like having heavy weight champion on your side. 

Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion

Instead, you book the asset and a liability and then reduce the liability each time a lease payment is made.The gain on the flip will come through as either short-term capital gain or ordinary income, depending on how regular, continuous, etc the flipping activity is.

Ultimately what I was trying to gain was advice on if this is a crazy idea or something that would be feasible and a good idea for me to try and get started on.