Hopefully it is bringing you some strong cash flow.

If you have a strong team of folks near the property (ie. handyman, HVAC repair, plumber, etc.) then yes, it can be managed remote.

I am certain that we can find something local that can work, it may depend on if you have specific criteria you need for bedrooms and location.Generally though, if you don't have a strong financial position, most people opt for cash flow first.

Many of the money-greats have been adamantly against diversifying because they wanted to focus their efforts into one arena, or just a few strong channels.

Also, taxes can be $3,500 for one building and $5,800 for a similar building turning a strong cash flowing property into a base hit.

I dealt with in the Boston rental market during December - February even though Boston is notorious for being a strong market.

That will affect your current ability to attract quality renters or receive strong reviews following their stay if made into a STR. 

I recommend you build a strong foundational understanding of real estate investing.1.

I think it comes down to you the investor needing to raise your financial IQ to be able to advise your tax professional on what to do so they can implement the strategy instead of them strong arming you into a conservative and poor tax play.

When you're buying a mess like this, covered in red flags, it should have strong cash flow to cover all the work and money you'll pour into it.Unless you know what you're doing, I recommend you walk away.