The challenge is that your capital gain significantly exceeds the $250,000.00 (or $500,000.00) tax-free exclusion permitted under the 121 exclusion, and if you sell your property the amount of capital gain that exceeds the 121 exclusion limitation would be painfully taxable.

Ryan Dossey  this is the exact reason these homes go through this cycle. you have  a new investor buying in a very challenging area.. the success rate for more than 36 months is no more than 50/50 ... if you want to see what your urban core rental will look like in 3 to 5 years.. well your looking at it when you buy it and it needs major reno... in my mind this is the province for very experienced landlords that have hundreds of these..

Not everyone would understand, but I've done this to get a better feel for future investing and the environment in which I will be farming.  

I'd love to hear the challenges you face selecting tenants.

We want to create an environment where people can come, eat great food and read great books.

We, together, are learning, making money, and building a great network of workers to get us through the present and help us build the future.Bottom-line: I think you need “pleasant nightmares” to grow, expand, challenge yourself, and ultimately create what you envision.

Investor-friendly, and looking for new agents.Super-low friction environment with strong agent splits, broker-provided leads along with sales training and support.Are you newly licensed in Massachusetts?  

Therein lies one of my challenges.  

When I put these together my biggest challenge is the lack of bookkeeping.

New and seasoned investors can meet and mingle, exchange ideas and refer business to each other in a more relaxed, yet structured social environment.