I actually just finished reading his book and was surprisingly disappointed for a couple reasons.

Happy to serve as a resource if you have any questions about the local market.

Since the cost seg study would just create an even bigger loss, it might not actually help you this year if you don’t have taxable income to offset.But here’s the part a lot of investors forget to consider—if you’re planning to buy another property this year, this loss could affect your ability to get financing.

I have the option to buy a 1,300-sqft 3-bed, 1.5-bath house in South End neighborhood of Stamford, CT, from a family member before it goes on the market.

If it is big enough that they could all fit in one side, then maybe she could still only charge her father-in-law $150/month and maybe rent out the other side to someone else.Her current house actually has a basement that could be finished into an apartment.

Large apartment complexes flooded the market with inventory and are offering crazy incentives and amenities that crush the small landlord which can make finding a tenant challenging and often for less than market rent. 

It's a good market with year-round demand that peaks in both winter (ski season) and summer (beach / lake / hiking / etc) season. 

I completely understand almost all of the frame work and bases but just need actual advice from someone one on on.

Great point about different states and markets having different laws about using evictions as a reason for denial! 

I am not saying you are wrong because I don't know the Cleveland market.