While they did a good job, I felt the price was steep, especially since the house wasn’t in terrible shape.I’m debating whether the cleaning charge is reasonable to deduct fully or if I should waive part of it as a goodwill gesture. 

Many people don't want to self manage from out of state, and professional managers can suck up alot of the cash flow, and not do as great of a job as you would've hoped. 

Maybe the 2017 tax and jobs act gets extended, but either way, if tax savings is the primary motivation, don't do it. 

It's important to understand the zoning/code requirements and obtain all necessary permitting if you intend on operating your real estate as STR anywhere in the country.

All good, he got the job and started on May, 10, 2018.To make a long story short. 

And service sector jobs and wages follow where those top-line incomes go.

If you want the furniture, just negotiate that and put it in the contract.Could you lease it from them for those 3 months and operate under their permit till yours is available?

@Victor Yang To use the rental losses to offset any active income (W2), you'd have meet Real Estate Professional status (which would be difficult to do with a W2 job because you'd have to work more on real estate than any other job to qualify) OR have an AGI of $150K or less.

From my understanding, as long as you intend on doing a STR when you close, there are no rules against changing your strategy after closing, especially if you find that something else is more profitable.So in our case, the lender determined an STR would bring in ~$3500/month (with all of their conservative factors), but now that we operate it as a huge 3300 sqft Co-Living property, it actually brings in $7000/month.

The issue is: can the operator survive to that "long term".