The longer you can hang around in Lawton, while you get comfortable with the industry, the better. 

I have house hacked 2 single family homes in Colorado Springs, moved out with both rentals cash-flowing very modest amounts annually, and am actively looking for the next property around Allentown, PA.My 2 options: Add to my portfolio and House Hack for the 3rd timeI know that house hacking will be the easiest barrier to entry around a big down payment, has the chance for a lower APR with a primary residence loan, and I am comfortable using this strategy as I have done it twice in the last 3 years.

What would you do if you were in my shoes and just starting out?

If you're not even comfortable driving up the driveway, definitely don't purchase the property.

If you're asking because it's going to be your first couple of problems, why not be the first couple of properties in the area where you live so I'm comfortable with and then boom then expand to another territory?

If you are comfortable with those numbers and you can wait it out until interest rates improve then go for it.You could also consider putting down a larger downpayment.

Then as you feel more comfortable you can start taking on more complex projects

Almost no one likes to sleep on a day bed - they just aren't very comfortable - so all you end up gaining is extra, unused floor space.

After all that extra time with your parents coming back around the holidays and giving yourself strong footing to have a comfortable life is worth considering. 

That is a pretty gray area that I don't feel super comfortable in but you may feel differently. 2.