Arranging schedule of various trades and balancing the good ones with the ones that are available.Permitting and inspection issues (should be a non-issue, but last house we had a new inspector that seemed like he had something to prove and nitpicked what I view as non-issues).Market swings impacting ARVs, or in the current market: are we going into a recession before the house can be completed?

thanks for the replies, to clarify a bit more, I'm mainly looking for an agent who can be my eyes and ears in the case I'm not able to be there in person to view the property.

I like this idea as I think it would give me a behind the scenes view of key financial aspects of investing. 

I’m currently trying to decide between two 3 bedroom units (one is roof top with gulf views and boat slip, other is ground floor with direct access to pool and big patio) , or a one bedroom in the same building that’s also roof top with gulf views (I believe sandpiper).

From their point of view, you are ruining someone's vacation, and can't be trusted to supply a good product (your property). 

I don't want to offend anyone or give them some sort of impossible criteria from their point of view. 

Also if you're in Zillow, another strategy you can try is to click the rent feature and click on properties for rent in the areas you're interested in and look at number of views + applications.

For example, if it's being rented out as two one-bedroom units but is only zoned as a single-family home, lenders might view it as non-compliant.

The home will already have a view of the water from the front of home and would be a superior view to the roof deck since it is on the rear of the home.  

From my point of view you need to separate work and investing by giving them deadlines and sticking to them.