It's critical to choose a strategy that works for him.

@Dielita McKnight If you intend to fix/flip as your exit strategy I would look into wholesale deals or try and get off market deal.

The properties in this area aren’t priced very high so this market should be great for the BRRRR strategy.

This is for just someone who puts the numbers in the boxes for you, most of them are seasonal, and you won't see them again - if you have an issue, someone else will deal with it in the future.If a CPA/EA isn't charging substantially more than these amounts, they are likely short changing themselves given they are often providing substantially more in services, guidance, strategy, etc.

I don't believe waiting is the right decision, but I do believe in putting together a strategy to maximize your opportunity. 

Other beneficial tax strategies would be a cost segregation study and bonus depreciation which would allow you to accelerate your depreciation and not have it set at 27.5 years. 

Seems like everyone has a bad deal at least once or twice in their real estate journey, no matter what strategy they try!

This is also a buy and hold strategy.

I see this strategy tossed around on here and quite certain the strategy is in violation of the loan terms.

Don't expect your CPA/tax professional to understand tax strategy with investment real estate.