Quote from @Sandra Morrison: @Shannon LeckingerI have STRs and LTRs - your condo will be possibly more of an appreciation play but you can’t pay bills with appreciation.

I would deny based on whether they had an outstanding debt/judgement to the prior landlord.

There may be other issues at play here that have little to do with a lack of experience at real estate tech platforms. 

Because the property is so unique pricing likely needs to be as well, maybe consider that based on the property needs/maintenance and location you may not want it consistently turned over so maybe you open 28 day slots and allow use with a 1 time per month turn over.

If you do choose to invest out of state, the best advice I could give you based on what I have observed running a local real estate group here for over a decade is build your own team.

I'm California-based where there aren't any real deals in my area, so I'm exploring Detroit as an alternative real estate investment market - due to the combination of it being a strong market and my having connections in the area. 

I'd underwrite the deal as any other - make sure you are conformable with the quality & tenant base. 

The bigger point is that if you use Walmart, Lowes or some other big box paint the base colors can and do change which will make touch-up difficult.

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

Better play it safe and use a warranty deed instead.Also, later on when you sell your property, it will keep the chain of title cleaner for the next title insurance.Last but not least, a warranty deed does not cost more than a quit claim deed...