As a newbie, I am interested in gaining experience under someone with plenty of it (via partnership or employment). 

I would rather sell the property at this point due to capital gains and the fact that my end goal is to generate about 12k monthly in passive income.

Yes the 100k profit, or whatever is left over after rehab (note purchase + expenses + rehab = cost basis) will be taxed and most likely as income not capital gains. 

This deed restriction shall run with the land; inure to the benefit of the city as well as to the benefit of the other residential property owners within the subdivision; and, be coterminous in tenure with the life of the accessory dwelling unit.

We are interested in purchasing property in the US in order to later upgrade and benefit from a 1031 exchange.

Are profits from wholesaling treated as short term capital gains then?

The increased basis will lower your gain when you sell if you are subject to tax.

I am a big fan of the less gentrified neighborhoods of Hermosa, Little Village, Uptown, etc. in addition to the Opportunity Zones with regards to capital gains tax deferrals.

Would you ever consider purchasing a house hack that has a small amount of negative cash flow (when considering all expenses to budget for, of course), knowing that cash flow would be positive once you moved out and gained income from the unit that you were occupying?

There’s also the huge benefit of using an FHA loan, but I’m not sure I would be able to sublet my apartment here in the city to occupy the property for the first year.Then, I think about the pros of having the tenants next door: they are next door.