Finding purpose and support for those involved that have "been there, done that" is the most challenging aspect.  

However, it could also cause more trouble as you expand your business.Where most small developments incite the greatest challenge is in managing projects.

Thanks in advance if you decide to the challenge.

Everything else you are talking about is only going to get yourselves into arguments, challenges and possibly even IRS issues.  

Take advantage of the free education and dont be afraid to challenge or ask questions.

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..

We bought our first 100+ year old house as newlyweds (read: naive children) in 1998 and have lived in and renovated several since, selling for a decent profit each time and learning how to do things like remove milk paint, do plumbing and wiring, and jack up a porch to replace failing beams.

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

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.