I live in the Chicago area and I'm ready to conquer.

I live in the Chicago area and I'm ready to conquer.

Doesn't seem like you've really conquered the market you're in and buying 1 house a year isn't a velocity that would justify needing to expand into another market.

After conquering that hurdle I find myself before the Biggerpockets community, looking for guidance from skilled professionals willing to bestow wisdom earned from experience.

 Natalie welcome the the world of Real Estate Investing, what markets are you looking to conquer?

Research enough to feel comfortable with a certain amount of risk and go out and conquer your market!

You and your wife can conquer the cosmetic stuff together and live in it for a couple of years.

I feel as though I’ve learned enough to conquer any challenges I may face, but when time is money, I think I’d rather not take that risk.

If you use your VA eligibility right now, then when you get to your next duty station and want to buy a nice home, you'll be what's called a 'MULTI user" and then over 3 points in VA Funding Fee will be stacked on your next VA loan.Here's what I'd do...or the subject property, since you have 10% down, do a FANNIE MAE  1st mortgage 80/10/10 = 90% Cltv)  purchase programEX:  180,000 purchase$144k  80% ltv - 1st mtg on a low rate Fannie Mae loan$18k    10% ltv - 2nd mtg (simo purchase money 2nd mtg) eliminates the PMIgives option to waive escrows you divide and conquer, meaning you can knock out the 2nd mtg. and drop total payment leaving just 1st mtg. paymentAlso, in lieu of a discount off sales price, simply negotiate seller credit to pay your closing costs (note: up to 6% of sales price seller concessions allowed)   

Ill just bet you can conquer both goals if you put a bit into it.