There are many post about setting up a vacation rental including  lists of items needed, importance of great pictures and descriptions etc.

Moreover, if the seller is resisting having the utilities on, I'd view that as a HUGE red flag (similar to how I'd view it if someone tried to sell me a used car, but wouldn't let me test drive it or even start the engine).Since correct and thorough due diligence is the foundation of successful REI, I'd be extremely hesitant to buy a property without testing the aforementioned items (unless the property was so heavily discounted that I could replace/fix all of those items if they turned out to be faulty...but even then, I'd be wary).I'd suggest strategizing with your agent on the best way to get the utilities turned on so you can do a correct inspection...Good luck out there!

Then 3) you will get ideas and necessary items from the Contractors that come to give you their bids.You will finally arrive at a complete SOW, but it takes a while.

I've noticed a few times there's drug related items laying around like bongs, etc.

If you weren't the policy holder, then you would have to get the person who had that policy in their name at the time (sounds like your brother) to file the claim and get things going.One other item to keep in mind is that you also need to know what the deductible is for water damage under that policy (if there was one in place).  

I was moreso concerned if it prevented me from writing off certain taxable items because the property was program assisted. 

Methodically eliminating every item on the inspection report starting with the safety hazards to cosmetic.

What you need to do is once you get that, find out how much it will cost to fix the items and then negotiate with the seller to lower your price.If house prices drop in the short term, it only matters if you plan on selling or refinancing. 

Only when I was for sure items 1-4 above were met, did I start the hunt. 

But in any case, you just have to make sure you are all on the same page about the direction you want to go or what you expect.You would probably need to look into how all the operations and legal and signature items will work with multiple members listed on the company docs.You mentioned needing to make twice the money, might be true, however half of something is better than half of nothing right.