Most people tell me no but eventually someone counter offers and then we start that conversation.

If i go through with this i would occupy one unit but eventually will move elsewhere and the plan is to rent them both out.Can you please let me know what you think?

Eventually they realize that they need to act quickly, and adapt to my way of doing things, but it ultimately benefits all of us, because I can bring them a lot of sales at full commission and I do a lot of the work!

I am interested in investing in general , wholesaling , owning rental property, and eventually learning to flip houses once I have more experience and money.

Yes eventually you'll run out of down payment money unless they are all true BRRRR's but you'll still stretch your money further this way and get the benefits of being able to leverage into more properties than if you were to just blow your wad as a down payment into a full market priced property in hopes that it will appreciate over time.  

I'm interested in wholesaling to begin with, and then I plan on doing some fix & flips and eventually get some rental properties.

- Some sort of owner-financing with the hopes things clear up eventually?

Eventually as my finances improve I would like to get back into multi family units for monthly income. 

(One of the leases is ending soon)i will be putting 20% down and my monthly mortgage/Taxes/insurance payment should be around $1400 or less.For the first couple years I will be owner occupying one unit but eventually will rent both out.What do you think?

(Residential real estate doesn't depreciate -- it at least holds its value)So while investors may break even on a cash basis (perhaps even lose slightly), their tax savings more than make up for it -- especially if they plan on retiring elsewhere & using 1031's to move their eventual capital gains to a lower tax state.Plus they also make their income stream more robust.