I realize the holding costs will be greater with a longer rehab period, but I assume it will be hard to rent up units while conducting major rehab work, while also reducing the efficiency of contractors ability to complete jobs in fell swoops...Thank you all in advance!

I am looking to house hack my first property around the Hampden/Upper Fells Point/ Remington/ Charles Village area and would appreciate any feedback on how to get started. 

Point is I fell for the let me buy you lunch line..

3 block radius of Patterson ParkRemingtonBolton HillUpper Fells / Butcher's Hill2 block radius around Bayview Medical CenterCharles Village South of Hampden (Wyman Park?)

That way I had multiple contacts/referrals in case something fell through, especially with contractors.When it comes to your questions, I personally scoured the interwebs like this site, podcasts/youtube, and others forms of educational media to gain a foundation of understanding and there is a pleurae of book recommendations as well people can always provide. 

I'm assuming the previous contract fell through based on what the WDO report found so financing couldn't be attained.

Which happens to be near Fells Point, which is analogous to the neighborhoods we like in St Pete.  

Not too bad.A few months into it and the tenet fell into hard times and could not pay the rent.

Today we were told that a former school teacher of disabled children, fell down the stairs the result of alcohol poisoning. 

It was about 4 acres.I looked at the property pictures and researched the area and just fell in love.