Can I list the higher rent but then agree to a monthly credit for her managing the property or is it easier to have her manage building for free in exchange for rent?

I've also met a few locals who have shared their wisdom and insights, so that's also been very helpful. 

Great insights @Ned Carey.

Any strategies or insights negative or positive is welcomed and helpful.

You might be able to defer them through owner financing or 1031 exchange (not sure how that would work if you have HML) but ultimately  you have to factor them in your investing strategy.

Two reasons come to mind:1) As a last resort after exploring a 1031 exchange, I would sell to get the cash to finance other deals.2) Retire to go traveling and don't want to deal with the tenants and bills.  

Any strategies or insights negative or positive is welcomed and helpful.

Here are my current options (beware, some of these may not make sense – this is my first time so I don’t know the difference between smart/stupid moves yet):A) Get property appraised and get a HELOC to use as a down payment for a property with FHA loan (2-4 Unit)B) Hope home value increases and sell when the equity >= a down payment on a 2-4 unitC) Remodel property and sell when the equity >= a down payment on a 2-4 unitD) Remodel property, Get property appraised and get a HELOC to use as a down payment for a property with FHA loan (2-4 Unit)E) Save money and wait until market rent >= cashflow, use HELOC/saved money as down payment for 2-4 unitI’m thinking option E is the wisest move but I want some other opinions to see if there's a faster way – any insight is helpful since I’m just learning.

Any insight to my mis-steps in logic or experience you've had in a similar situation would be greatly appreciated. 

Thanks very much, I appreciate the insight!