Hey there – I bought in Trinidad last year for the exact reasons you mentioned. I was priced out of every established neighborhood and did not in any way want to live in MD or VA. Was looking for a great investment home in a transitional neighborhood walking distance to restaurants/bars and the city in general. I am a single woman and I live along West Virginia Ave. You can probably guess which house is mine if you drive up WV b/c its the only one that is painted! Screams break in to me but alas…. I might just be projecting b/c I am wanting the same things for myself (great investment, turning neighborhood etc) but I really enjoy living there. Yes, you have some very “interesting” people but I have had no problems in the year plus since I have lived there. Just a couple really interesting conversations 😉 It is rapidly changing and I have found my neighbors who are all long standing residents to be quite lovely. They really look out for me which I really appreciate and it does have a community feel to it even if some of that community are seemingly a little sketchy. They aren’t for the most part. In the year since I have been there I have seen homes going for $100,000 over what I paid for my fully renovated house so I am seeing the investment piece come true. Yes, it is block by block in terms of crime and houses that are either abandoned or severely in the need of work. The house next to me for example is abandoned and a true eye sore but I have heard rumors that it is about to be renovated which is super exciting and only increases my property value. The farther north you go, the worse it gets but again I do strongly believe it is changing. It is close to H street, Union Market, NOMA, metro, union station, streetcar etc which I think makes it one of the better “transitional” neighborhoods left close to town. I would love a new neighbor so DO IT!