The only time I would suggest buying a condo, if you are in a high appreciation market + the rental market demand is high in that area.

Since you are just graduating college you may already realize that it's not what you know, but who you know (as a personal note, I had college friends that were barely passing their classes however they ended up with really good paying jobs due to "who they knew").

I'd suggest you define your qualification criteria and publish it in your ad and follow HUD screening best practices from there. 

I always recommend investing in areas with strong underlying fundamentals: jobs, limited housing supply, desirability/ high demand, population growth/ net in-migration, affordability, etc.

That bathroom will be a full gut job.

Have a lower monthly payment, not pay PMI, be able to save a bit more from the W2 jobs each month, as well as having a greater percentage of the mortgage covered by the upstairs tenants. 

As long as the job gets done right, they shouldn't mind who's doing it.

There is a whole lot to dig into but I figured I'd start with introducing myself as that was suggested.

If that makes it worth it for you I would suggest to go for it! 

I find that automatically sending a message to your new guests is very useful, you get to start a conversation right away and it increases the guest's experience.I also automate all my cleaning jobs with Turno that I find invaluable.