Their agent was solid so that's why we decided to work with Empire Property Management, their sister company, which ripped us off on the PM aspect of the business by frequently and overcharging us on many maintenance requests (they have their in-house contractors).

on the renovations aspect of things I too will be getting my hands dirty.

They should have their agent send you a certificate showing that they have General Liability (for Bodily Injury & Property damage) and  Workers Compensation. 

So I'm between Homestead's new market, chance of appreciation, and more bang for your buck aspect OR Tamiami demand for rented rooms. 

You have to be purposeful and design every aspect of your rental business to run with minimal input from you as the Landlord, so if something happens to you it can be easily maintained by your spouse, kids, or home office. 

I asked her if she would allow couch surfing and if her parents would be happy to be paying for that type of squatting.I think you have far more serious aspects to worry about if you’re taking on the hard and unrewarding work of renting to roommates.Why not include all rooms in this.

@Anita AnandHi Anita, Iike many I struggled with some of the emotional aspects you mentioned.

Of course they will try to move you into KW so weigh cost/benefit if there is an aspect of the business KW has a training for that you’d like to attend, go for it.

Utah REIA - Presentations on different aspects of real estate. 

IMO the most important aspect of a great investor agent is their network.