Hello, similar to Steve and Sean, I have an existing Stessa account that I would like to link to.

I’m over here on Big Island, up in the Kohala coast, and it offers some resort areas too on the sunny western side similar to Ko Olina on Oahu.So things to consider are:- Which Island- Your budget- Will you be financing or paying cash?  

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

A friend of mine in San Antonio had a similar situation.. she inherited a vague commercial lease and learned that the rules differ big-tiime from residential.

It will only appraise based on comps of similar residential properties.

Some states are dealing with similar issues (wind, hail, fires, etc.), while others are working through some completely unique situations (like CA or FL). 

The Detailed Engineering Cost Approach is generally used for newly constructed commercial buildings.DETAILED ENGINEERING COST ESTIMATE APPROACHThis approach is very similar to the Detailed Engineering Cost Approach, with the difference being that if there aren’t records for specific costs, an estimated cost is used rather than the actual cost.

If not then just go on zillow and see what similar apartments in the neighborhood rent for.

Freddie has similar intricacies, but also does not require a two year history of receipt; https://guide.freddiemac.com/app/guide/section/5306.4If you can use the rental income to drive the DTI down so that you can reduce the down payment similar to that of the FHA product, the benefits of the conventional option will outweigh the FHA option, as I'm assuming you have a strong FICO based on rate quoted with no points.  

Compare other rentals with a similar size, location and bedroom count to get an estimate of what the rent would be while you're living there.