They may sabotage the sale by complaining about the HOA or that the cabinets are cheap or utilities are expensive.It sounds like your tenant is a good one so it may not be a problem.

Any investers/real estate agents in that market willing to meet with me so I can pick your brain and compile a pros and cons list???

I want to hang onto this tenant as long as I can since they are literally the ideal tenant however given that they may want to utilize a smaller lease term I need to insulate for vacancy and turnover cost.

That being the case, I'll be spending a bit of time on here to see what wisdom I can pick up. 

Then I set up Cozy to collect first months rent online and utilities must be transfer to their name before handing over the keys.  

One thing I’d add to the list is that utilities typically aren’t on which is risky + a major pain when you transfer title.  

Assuming you have net rental income, the rental expense would be picked up as income but your rental expense (personal) is not deductible, so you would be paying taxes on the income that you paid yourself with an after-tax dollar.

Residents pay all utilities as of now and commercial pays own water as well. 

@Anita MuhammadOne of the reasons why I picked real estate investing and self-managed local landlording as my way into real estate investing is that I was kind of born into it -- my grandfather ran apartments this back in his day and I grew up on stories told by my mother about the life.

(Delaware or Maryland)   which would you pick and why?