How to determine how many investment properties to buy

[Andrey Y.]

First of all, I really do appreciate all the helpful guides and discussions on here to help educate a new REI such as myself.

We can all invision the statement "It is better to purchase 5 properties at 20% down, and finance the rest, than purchase 1 similar property cash."

I realize there are many variables such as long term goals and market, but I am trying to get your opinion on this. This is for BUY and HOLD type investing. If you had the cash, would you start with putting 20-30% down on a single property, and look for several more in the coming months?

For the most part, buy and hold investing is tricky in Hawaii when demand is high and rental income is not great compared to purchase prices in a currently seller's market.