I hadn’t thought about the risk of expanding my portfolio by having multiple properties over leveraged, although that seems to be a growth strategy that many use,  I’m not sure it’s one I’m comfortable with.  

If you want more, you buy more at a pace that is comfortable for you.

Feel for you and your neighbors.

This upgrade not only improved comfort but also significantly modernized the property.

A primary residence will most often provide more favorable loan terms so if you are willing to wait one year while you living in your new property and are comfortable with renting out your primary residence to a tenant, then getting something such as an FHA loan is a good strategy to minimize your upfront costs and hopefully get better loan terms.

It’s worth looking into now to get ahead of it, but also depends on your comfort level and goals.

I'll echo what Zeke mentioned about interviewing multiple realtors / PM's / Contractors to make sure you can get a good idea of what the area is like, in addition to working with someone you're comfortable with. 

What is your comfort level? 

This will impact your costs and time commitment.Risk Tolerance: How much risk are you comfortable with?

Not sure if that's much help other than to let you know you're not alone in feeling that way as a newbie.