It's hard to walk some days now, there are other days when the pain is ridiculous, but so far, I've managed to keep the walking up.

You need to value your contracting work honestly and then separate that value from the value you provide managing the process as the boots on the ground. 

So, if you're discussing business matters with your property manager or realtor during a meal, those expenses could potentially be deductible.Be mindful of distinguishing between personal and business expenses.

My property management software creates it for me. book.suprcap.com

The tax code defines a real property trade or business activity as “any real property development, redevelopment, construction, reconstruction, acquisition, conversion, rental, operation, management, leasing, or brokerage trade or business.”2. 750 Hour TestYou must spend more than 750 hours participating in real estate business activities during the tax year.

Rougher neighborhood but a side of town I am familiar with plus I would have a property manager managing the property.

They seek out skilled professionals who can offer expert advice and solve management issues.Real estate agents are drawn to property management companies that use smart technology and new tools.

They might be able to do property management there but it would be quite interesting to see what your cashflow could by renting by the room.

Your loan probably technically doesn't allow this because there is a "due on sale clause" but I have never heard of a loan being called as long as it's being paid My advice to you would be to screen potential property managers, read reviews then set it up to be managed by them. 

I know I’m breaking the fundamental rules here of property management, but should I stop putting up with this?