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In addition to my surrounding area of Bridgeport, I am also open to looking in New Haven County, Middlesex, and Hartford as well as an out of state market (Detroit, MI). 

If your property went up in value, overvalued, more than surrounding properties, you should contact your tax assessor and get the forms to  file an appeal.

Yes, you bought what seems like a good deal on paper, but in reality, you own an old apartment building in a neighborhood with poor security, possibly surrounded by long-vacant shops, streets piled with garbage, and a poorly managed community.

Look into Columbus and surrounding areas.

While cash flow can be limited within the downtown area, there are still excellent opportunities for cash-flowing rentals in surrounding regions.

Denver and its surrounds have particularly active markets and a lot of active individuals offering ancillary services so I'd suggest you research those available services you're looking at offering to help you get an idea for what is well covered, what is lacking and what your competitor's pricing looks like.

If there are any community members that are local to Westchester County or the surrounding area and have time to meet up and share experiences and tips, or even have projects themselves that I could provide some help within exchange for the guidance please let me know!

I would say the surrounding neighborhood is a B-.

I see a lot of new construction in Richmond and Berea as I travel from Lex nearly every day im excited to see how the mega site in Mt Vernon and Richmond grow these areas What surrounding areas of Lexington are you seeing more activity?