High mortgage in good area vs low mortgage in less than area

[Ruark Adam Barrientos]

I’m in the Military and I’m in the process of moving to the New Cumberland/Harrisburg/Carlisle, PA area and I want to purchase a multi unit property and house hack. Given the current real estate climate, is it better to purchase a multi unit rental property with a higher mortgage in a more desirable area, and enter into potential bidding wars over the asking price, or is it better to buy in a less than desirable area and build my portfolio and cash flow? I want to begin and can go either way, but I’m not sure which is the better route.

I imagine it may be a 50/50 decision but does anyone have any lessons learned that they could share and/or things they wished they would have known going down either path or both? 

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Quote from @Ruark Adam Barrientos:

I’m in the Military and I’m in the process of moving to the New Cumberland/Harrisburg/Carlisle, PA area and I want to purchase a multi unit property and house hack. Given the current real estate climate, is it better to purchase a multi unit rental property with a higher mortgage in a more desirable area, and enter into potential bidding wars over the asking price, or is it better to buy in a less than desirable area and build my portfolio and cash flow? I want to begin and can go either way, but I’m not sure which is the better route.

I imagine it may be a 50/50 decision but does anyone have any lessons learned that they could share and/or things they wished they would have known going down either path or both? 

A building you spend $300,000 on today that goes up 10% is worth $330,000 tomorrow.
A building you spend $500,000 on today that goes up 10% is worth $550,000 tomorrow.

That's about $220,000 difference.

Since I assume you are using a loan, VA or otherwise, you aren't putting $500,000 cash down. So, your leveraged return is fantastic, especially on the higher priced property.

Buy the best, highest you can comfortably afford if it has cash flow. Don't buy an expensive property just because it is expensive if it doesn't cash flow. You will end up losing it if you can't pay the mortgage.