I feel pretty okay about it, but it's partially about your comfort level and risk tolerance (and probably the value of each property).  

In the residential world, some requirements are relaxed comparing to commercial so it's up to you whether you want to spend the money to have a better planning versus skip the planning and perform the work impromptu.

- Nobody in here is comfortable answering this question. 

I was still looking for homes I would personally be comfortable in. 

If you are crushing it with smaller deals and find comfort and ease and low ROE (Return on Effort), then stay the course.If you want to scale, you may have to find a partner to help with capital and balance sheet.

Certainly open to other ideas and strategies, it would just require additional diligence from my end given my level of comfort and expertise would be lacking in other areas.

Parents recognize this and are comfortable/agree.

.🌱 Whether it's painting, hiking, cooking, or playing an instrument, hobbies give us a chance to relax, get creative, and just feel good.🧘‍♀️ And here's the kicker: hobbies are like natural stress-relievers.

If you have experience in managing construction, then you should feel comfortable filing an Owner Builder permit.

Since your experience level (1st investment) is very limited, I'd speak with some title companies to get a feel for comfort level in working with them.You'll be asking a bunch of questions (you should!)