I started into it after 20+yrs in the trades, I was a master journey carpenter already and I still had tough reno's, consider that. 

These locations should be in dense trade areas with solid demographics.

And if you do put someone on your 'team' then do you trade them or dump them when they do not work out? 

Also, with eviction moratorium in place many tenants will decide to live rent-free for the next 4-6 months or maybe even longer.YUP in the GFC you had stratigic mortgage defaults  IE people could pay if they wanted to but they were underwater and in non recourse states traded bad credit for living for a Very LOOOONG time for free in their home..

How quickly and efficiently can I work in different trades, what small things can I do myself to reduce that time line, and what materials can I use to prevent this in the future. 

If they're not interested in selling to you at a discount, trading equity for speed and convenience, you're wasting your time. 

House hacking is always a bit of a trade off, and if you truly want cash flow you will probably land in a B or C class area instead of the "A" areas. 

Wholesaling = job aka trading hours for $s

You can do up to a fourplex with a regular conforming loan.Another thing to keep in mind the closer you get to a major city, you are are trading cash flow for long term appreciation.

There are a few companies that will bring you on board so you can learn the trade in a protected environment.