My plan for this year is to remodel and upgrade the house to then put it to cashflow either via short/long term rental.

What is the risk there?  

It insures all types of risks but does do a nice job with rentals in many markets

Coaching can absolutely 10x your business, but theres always a risk of a bad experience.

That literally makes no sense.Who is at risk of any harm for str's?

AirBNB is a platform where you list a short term rental.Next, like others have said, it is a pass through cost and you should simply put in what the cleaner charges.

Are they going to be able to buy your proudly done flip.3) If you misjudge the market, do you know when to dump it.4) Can you put a spreadsheet together on your purchase costs, carrying costs, rehab costs, closing costs, selling costs, tax costs, contractors that don't show and delay your project etc. etc. etc.5) Is the return worth the risk.

I will be putting more thought into these. 

WE all get paid at the same time when the property closes I get my money back and my agreed on captial partner split they get the rest.. for some it works great we help them scale.. for others that just do a few a year and are dialing for absolute cheapest rates and have the money for downpayment and to make payments etc.. thats the route they will go usually broker who is putting them into a large lenders program and raking points off the top and at closing..

As repeatedly advocated on BiggerPockets by myself and others, house hacking is one of the best forms of entry into real estate while mitigating risk.