If you can lease it quickly, you know the market, you know how to get to restaurant decision makers locally, then it may make sense to do it yourself; however, if the leasing function cuts into your time for your primary job, then probably makes sense to outsource it. 

I'm blessed to work from home with my current job and that has allowed me to spend more time with my family, but it'd be fun to not worry about our finances as much and be able to take more trips and vacations.

Due to the nature of my career (I'm an economist with a tenure track job), I have fairly idle summers.

I will need to use a manager on this one as it is about 45 minutes away and I have a full time job. 

If he doesn't meet the criteria, you can move to evict, or you can give him a chance until he is unable to pay rent.But, if he was doing a good job, why not keep him?

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.