I suggest using a service like Mayistay.

Can anyone suggest Property Managers in the Columbia, SC market?

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.

Denver and its surrounds have particularly active markets and a lot of active individuals offering ancillary services so I'd suggest you research those available services you're looking at offering to help you get an idea for what is well covered, what is lacking and what your competitor's pricing looks like.

Thanks in advance for the recommendations / suggestions!  

All of the things you suggest are options to the beneficiaries. 

Cities don't play fair when they decide to go after you.One thing I would also suggest you do is look on AirBnB for the specific building you want to buy in. 

You can read a book and multiple books, but unless you are out there doing it (I.e. getting bids and getting contractors to truly get you an exact estimate) you will be far off from the numbers you want and may even lose money on the flip/rehab.The best advice I would suggest in my experience is that you should get into the line of work by either partnering with someone or working with someone on some projects prior to going into a flip on your own.

Here's an article with additional FAQs on cost segregation studies that you may find helpful.

Thank you for taking the time to make these suggestions!