I'd mitigate the worst case by not going over $150K on purchase price.Also, it looks like you have some money, so even in worse the worst case scenario, you could sell and sustain a loss without sinking.In the expected case you will invest about $200K and earn about $20K, a 10% ROI.  

I want to start investing there to increase cash reserves however I have an end goal of buying and holding multiple properties that are free and clear in order to sustain a comfortable, but not lavish, lifestyle for myself and my family. 

Sit down with them awhile and do some detective work, too, like actually call insurers, trash and utilities, mortgage brokers, tax authority, etc...Your calculations will only be as good as the raw numbers (and I find sellers may give rosy estimations sometimes, rounding income up and expenses down)...

FHA is very picky when it comes to 3 and 4 unit MFHs making you prove the income from other units will sustain the mortgage which gets difficult since you'll be living in one of the other units and the LTV will be really high.

Lots in streeted/ utility areas are only worth 5-7K$, huge supply.

.- it's always good to see another Hoosier utilizing this great site!

Right now I'm just looking To flip the land.The property is 14,000 sq/ft with sewer & utilities at the street surrounded by very similar lots & houses in the neighborhood.

I never noticed fire hydrants until I worked with public utilities, now I spot them everywhere and can rattle off the brand and (approximate) age without much difficulty. 

As others have said, it's probably best to utilize your money buying one or two multi-unit buildings. 

@Jon S, most of the issues I've seen boils down to HOA / code enforcement / underestimation of utility usage.