the lady I talked to said it counts against you when you do something like going from an IT professional to say something like auto mechanic because you're changing fields.

., professionals who are in the area for a year for work and want a large space to rent for that period.

Went to college for architecture and have worked in my professional life as a building inspector, insurance underwriter, and actuary, and I lived in a 2-fam and had two more 2-fams in my hometown of Buffalo, NY, and sold those when I got a job offer and moved to New Orleans, LA. 

Readers are advised to seek professional advice.

They focus on deals in the gentrifying areas of town, and target higher end tenant base they have built through professional networks. 

Now I’m not worried because o have automated online systems for rent collection, contractors and licensed repair professionals on speed dial, and I have some boots on the ground in the form of family who can lend their knowledge and keep an eye out for me.My first thought to this question is : if I’m worried that it may be too far ,then for me it may be too far.I could never do a flip that far away, IMO.

If your property is zoned to allow an ADU (and this is a big IF), then ask about regulations for short term rentals. 

Other things you can use to demonstrate your intent would be your normal practice, rental agreements or rental listings, written correspondence with your professionals etc.You've got a pretty healthy gain to shelter for sure. 

First, tell you boss at your company and make sure it's okay -- it doesn't do any good to make an investor mentor if you also lose your 9-to-5.As for approaching the individual: 1) explain why you're interested; 2) say that you did get the ok from your company, and that you're doing it in a totally private not-related-to-your-company way; and 3) offer to help out with his properties like you said.A key thing to be clear about -- if you offer to do any of your professional day-job work for him on the side as a favor for him helping you out, you need to be sure that your company doesn't mind you doing it.

Attorney is the best practice professional to help establish buy-sell agreements and other exit strategies, including provisions in your partnership agreements.