If it's a sandwich lease, negotiating skills come into play. 

I need contractors in all trades.

Focus on that, and develop those skills.  

Mostly DIY with specific trade professionals.My goal is to obtain cash flow to build up my portfolio and ultimately get time back from my W2 job.

Maybe the cost can be justified, but you should expect transparancy on what exactly was done etc.Being a PM is not easy, owners expect work to be done by a skilled and licensed contractor, who of course gets a salary, also benefits and work truck, not to mention a mark up for the PM to actually make a profit. 

Q1 Answer - If a rental is a trade or business per IRC 162 it qualifies Q2 Answer- STR is passive on E if over 7 day average rental stay and no substantial service STR is non passive on E if less than 7 days average rental stay and no substantial services. 

This is important for people to understand, so they don't confuse their luck for skill.

Ect are business often very skill and work intensive business’s not passive investing.) returns on investment out there.

I don't know your strengths, weaknesses, or experience level but when I started I had a few skills, but more importantly I had motivation.

That would have put me into an area where I wouldn't feel comfortable and I'd be trading the short term stress of 'shoulda could woulda' with the long term stress of 'am I gonna be able to make money on this?'