My main concern is getting stuck with unforeseen maintenance or repair costs post-purchase.

Seems like everyone is pushing Columbus, OH, Indianapolis, IN and other similar towns/cities.  2.

If you are developing the land which presumably will benefit the City, assisting in bringing a city utility line is something in my experience they will help on.  

I only have experience in my own primary residence, I have perfect credit, zero revolving debt, wife and I both work very well paying jobs, with the one main difference in that she actually likes her job, haha, and I'm striving for greater things for me, my wife, and my 2 young boys.Nobody in my life seems to have such higher aspirations, so it's tough to even have a conversation about such things with any friends/family without blank stares.Any advice either of you can share to point me in right direction, or just a 1st step suggestion, would be incredibly appreciate.Thanks!

My main thing is that I know I need to sell my properties to scale my portfolio, but I want to keep the interest rate and I'm not that knowledgeable about multi family yet so maybe I'll make the jump in a couple years when I have increased my equity and am very comfortable with the multi family market.

If your main goal is to supplement working full time I would purchase as many properties you can in a different state instead of paying cash for one property. 

I've selected some cities to compare and I'm trying to find some sites with market data.

Hi Shawn,Thank you for taking the time to respond.I’m waiting 1.5 years mainly because my plan is to locally house hack my first or few properties, and I’m unsure exactly where a job will locate me post-college.

@Alex Lee, it depends on the lot size and more importantly, the County/City ordinances.

When it comes to borrowing money to purchase an investment property or primary the main 3 things to focus is assets, credit, income.