In summary, the deal has to make good economic sense first, then see how to be the most tax efficient.

Yes many flippers try to do the work themselves thinking they can get it done cheaper and because they can't find professional, reliable and appropriately priced contractors that know what they are doing and get it done efficiently.

In addition, we also have investors (currently, about 20 active and 50 potential) and we're looking for a simple tool to keep in communication with them as wellDo you have any suggestions for something that's cheap, easy, and fits these criteria?

With a golf course, that seems kinda hard to do outside the active season.The two might go together well, if they can efficiently share some resources (ie, kitchen and staff).

Its not LA or NYC where an efficiency apartment can be rented out for $1500/month.

Feel free to PM if easier to communicate.

It probably doesn't hurt to frame communication with the tenant as if there was a 3rd party involved in decision-making. 

@Alex FreeloveI don't think @Duc Ong is giving you tax advice, the ratio (ROE) that he mentions has to do with how efficiently you are using your equity (tax implications aside).

You're thinking long term, which is great, but that means all the long term CapEx items are going to catch up with you...one more reason to limit your time with SFR and aggressively move to MFR where you can realize efficiencies of scale. $150-200/unit/month is probably more attainable.

A good property manager can be hard to find —but finding one who can efficiently manage your rentals will make your life significantly easier.Handyman—You’re going to need someone to take care of the little things that come up on a daily basis.