Two years ago I purchased this beautiful three story 10 bedroom brick foursquare in the North End of Hagerstown, on a historic tree lined street (Oak Hill Ave). I purchased at 305k with a 60k down payment from the proceeds of my previous live-in flip (this is only my 2nd purchase, so I'm still new at this!). Now that I'm beginning to tackle renovations using income from my day job, I'm stuck trying to decide whether to renovate to flip or renovate to hold? With 10 bedrooms and a huge basement that could turn into a studio apartment there's tons of rental opportunity here. But, what about my neighbors? What about compliance with city regulations? What about separate metering? So much consideration goes into turning a single family into an apartment building essentially. And, it'll be my very first time landlording if I go this route. On the other hand, the house just across the street recently sold for 445k, and another is being listed for 499k a few blocks down. Both homes show very well (not flips). The first is 1,000 sqft smaller, while the other is 300 sqft larger. I believe if I put between 30k-50k into quality upgrades (I do most of the work myself) I could possibly sell for 500k or more. So, what would you do BP investors? Anyone familiar with the Hagerstown market please chime in!

*I'd like to quickly add that my ultimate goal is to utilize a combination of judicious flips and long term rentals as a vehicle to build enough passive income to quit my job and finally LIVE. Thru completing my first live-in flip I've realized a passion in the flipping process and would continue doing this as an additional wealth building tool. I would like to be able to do this in the shortest amount of time as possible. Any guidance is sincerely appreciated.