It is very difficult to execute as there are so many moving parts and people involved. if you do a few buy and holds first, test out contractors and slowly build your team you can prepare yourself to take on deals like this. 

I'd look for signs of arcing around those outlets.Other things I look for are how is the foundation, cracks in the walls (assuming lath and plaster), condition of the mechanicals, depending on what the house is built on, I may get a radon test done for the air and water (near me there is a lot of ledge, so radon is an issue in most homes). 

That said, do ask yourself before signing on the bottom line: if this tax strategy fails the IRS scrutiny test - what happens then?

It isn't helpful that you are not able to really test out Hostaway without paying a $250 onboarding fee and paying for the first month of service.

Now is not the time to “test the market” with an ambitious price to “see what happens.”

I believe your numbers and your forecast which a lot of the rosy numbers posted do not pass the sniff test on being achievable.  

Agreed on the 4 pictured one - just wanted to test out and see if it would help.

Start-up costs are also deductible but are amortized over 15 years with a limit of 5k.Start-up costs have strict rules and your case might not be the same as this one.Case Summary:Timeline line of eventsStarted investigating property: FebPut first contract (canceled): MayBought first property: December 30thWhether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business:Whether the taxpayer undertook the activity intending to earn a profit;Whether the taxpayer is regularly and actively involved in the activity; andWhether the taxpayer's activity has actually commenced.On the basis investor testimony, we may assume that he undertook this activity to make a profit and that he regularly and actively engaged in it.

B. tested the unit to see if it's actually defective.

The approved contractors have to meet insurance guidelines (often not met by an average company), typically are certified by national and state agencies in home energy efficiency, and invest around $10k in energy testing equipment just to participate.