This is a real estate group so I’d assume a lot of people own a lot of real estate.

I've trained people at my jobs when I was a senior accountant to controller.I've used Yardi Enterprise (old desktop client software)Yardi Voyager 6s & 7sYardi Genesis2Reason why I say you won't be able to find a tutor is because no one is going to spend $15K a year to use as a training platform to mentor and tutor people.

With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

This is one area where it helps tremendously to have per-existing relationships with people in the industry such as family or friends.

If the applicant comes from the pool of people that I or my tenants know, I use real estate as a way to give back as many of my tenants will not qualify credit wise or may even have a criminal background or would struggle for another reason if I were to just stick to the "background/credit check" criteria. 

Does anyone have experience employing out of town people with 20 plus years experience ? 

Some high and lowlights:- I had one tenant that brought German cockroaches in and then blamed it on me- Same tenant asking if her daughter can visit but failed to mention it was 5 more very noisy people- another tenant having constant loud arguments with his gf- tenant saved some of my stuff when the house flooded due to a pipe burst and another time during a monster rain storm.

I still recommend people give it a try and see for themselves.  

One other thing that people in their 60s can consider is - if you are planning on taking Social Security and making passive income part of what you live on, rental income may not count as income against your Social Security benefits.

It's an asset that will continue to grow as more and more people and institutions begin to adopt it as a safer hedge against inflation than precious metals.