Wanting to lean on some of fellow investors experience when it comes to technology that can help provide leads/ gain some insight into leads.

I would not include appreciation since that is an unrealized gain.

Is wholesaling a good first step for gaining experience?

Value $900,000; $600,000 debt, $200,000 basis; 7% sales commission, only him- mother is deceased- $250,000 cap gain tax free, $70,000 sales concessions or repairs, capital gain tax on $550,000 less costs,  etc etc.  2 out of 5 year rule, can he live in other buildings?

I want to buy him out because the property has a 3% mortgage rate, has gained 100k in equity the last 4 years and cash flows 1k a month.

The next phase of my maturation cycle is gaining "on the job experience" in the form of GP participation before attempting to take down a deal by myself. 

I like to keep things simpleEIther sell him 1/2 the share directly(Look to see if you can defer your gain/tax.Or look to become partners in a new property.

Hoping to gain some confidence and knowledge in the BP community! 

Usually holding costs and lost opportunity costs far outweigh the gain in sales price.I would also have multiple exit strategies and if prices dropped more than I wanted could I keep it as a long-term investment and have the rent cover my expenses.

However, if you decide to sell after holding the property for over a year, you could qualify for long-term capital gains tax, which is lower than ordinary income tax.