You can usually use bonus depreciation against the asset assuming it will follow the short term rental loophole rules of 7 days or less average stays. 

Am I better off focusing on doing a flip or wholesaling rather than doing a buy and hold?

Other than to negotiate as hard as you can. 

Hello,I am new to investing and I lack knowledge of how to use my passive losses from rental properties. or more than lack of knowledge, I just don't think my CPA knows this topic well.  

So the thing about the roof is that it continues down such that it's much lower to the ground than the third floor windows. 

Land Use attorneys are usually engaged for large, complex developments (although, again, maybe that's the norm in your market; I'm in California).

It is going to be harder than you think.

I know this was my mistake for not getting them before sending the money he requested (he'd done a couple rehabs for me before and it wasn't an issue). 

Personally I’d try to stick with 1-2 projects that had a potential for higher margins than to try to scale up and need more workers and more headaches.

Can I couple my residential loan with landlord insurance?