You should have a minimum square footage of home (and possibly a max), minimum bed/bath count, location specifics (can be multiple locations), type of properties (standard sale, REO, short sale, probate, etc - I go after them all), and your price point of $250k should have a specific range, for example $100k - $300k.

You may be counted as high risk with the multiple loans, so financing in general may be difficult depending on your current income.Also, if you haven't already, take a look at what the current leases are renting for.

A multiple member LLC is required to file a separate return. 

thanks @doug pretoriousI like that approach of multiple options.

Right now everything is getting multiple offers, so putting it on too low isn't very risky as long as you ask for highest & best.  

Aloha Daryl - investing in real estate is definitely a worthwhile venture, especially in Hawaii where the price points can make one deal the equivalent of multiple deals on some mainland markets.I want to give you some friendly and constructive advice.

With that being the case, should I be looking at taking out mortgages to buy multiple multi-family properties? 

Make sure you are putting your ad in multiple sites, newspapers etc.  

I would love to find an apartment so I don't have to find multiple deals.  

I love the idea of acquiring multiple properties with cash refi's and then use the cash flow to snow ball your debt.