Pittsburgh is very affordable and you can get a deal in the price range you are looking but again do you have the resources and the people in place to get the job done is the question.

Then, after either my husband or I goes part time with our W2 jobs, begin the short term rental conversion. 

Within 2 weeks of me showing up everyday the contractor was suddenly finished and left the job site.

If you and your partner are planning to self-manage and keep your full time jobs (for now), I'd stress the importance of proximity and convenience to your investment property. 

We have a rental portfolio with five kids, travel sports, and a 60+ hour a week job. 

This means jobs.

He just finished his last job and he is refusing to leave the property and is squatting stating that I will have to evict him. 

Are there any ways to secure financing on investment properties without a typical 9 to 5 job?

Assuming you have no other major obligations or constraints (i.e. family, job, finances) guiding you and could pick any place in the USA to move and build/start a real estate portfolio, which city would you start?

I think I have enough career stability that I could always find decent -paying work if I lost my job for some unforeseen reason, and of course my husband can always work more.