I’m licensed contractor 3 states and have crew and skill set to handle the task.

With your combined skills, one very good way to grow your portfolio can be simplified as buy 2, sell one, rinse and repeat.  

@Rebecca Seidler what your skill set and goals are it actually has very little to do with the house and more with personal style.

Assessment of where you're buying and its 'frothiness factor'2 - Your need for cash flow vs longer term appreciation/equity building, mainly will depend on your time horizon with owning the asset3 - Your skills/ capabilities - some people are more naturally geared towards handling lower class areas, tenants, and usually the items that come up maintenance wise with this.The advice I usually give to 'youngins' (I'm 36 by the way) is to take the long view - which means the equity building, and your TIME to continue focusing on your career, building skills, etc - would lead me to be biased towards the property that you felt would hold / appreciate in value more over time.....

Changing an entry knob or a deadbolt is one of the easiest basic handyman skills to learn.

Sweat equity seems daunting being as I am a pen-pushing millennial with no handy skills as well as spending all too much time at work. what are your thoughts?

When I got laid off, I saw an opportunity to try to educate myself with alongside a partner who is skilled in rehabbing.

If you don't want to wait, I understand but I need to know today, because I am going to rent it to someone else if you're unwilling to wait."

What I have found though is they are too slow and too expensive to do too many lien searches and sometimes not all that skilled in helping you figure out areas of concern on a property you don't own.You might check out a site like https://www.titlesearchdirect.com/ and see if that helps.

The economic and demographic trends are week and the city has been unwilling to invest in infrastructure and economic development.