Logan A.For asphalt shingles, 2 previous roofs + a new roof = 3, which is the most any respectable roofer will put down.  

I think the sweet spot for rentals is in the $125-165K tax range.

@Roy LhanieWhile I respect all the great recomendations from all the comments, I will rather settle in and learn FIRST, before decindig where to invest.

Kind of a large range. 

I would buy 2 or 3 rental houses in the $20-30k range, wholesale, then save the remaining balance for a safety net.

Yeah, its tough competing with so many cash buyers in your market, especially when you are in a lower price range. 

For example I just sold a beach house and all the comps were in the mid to high $400k range.

Some are more expensive than others (HOA) fees, some have central water and sewers while others have well and septic systems; most all have recreational facilities; you will find a wide range of prices, dues and taxes.  

Condos in my price range on the other islands just don't command the same kind of high nightly prices that I can get in Waikiki.

Your purchased list would probably have filtered out that price range and thats what I am talking about.Your list should contain ALL properties where there is an opportunity to buy a property that needs work.