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.

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

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

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. 

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.

Here's a quick test... call the company yourself, see how long they take to answer the phone and how they answer the phone.

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

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

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.