I’m not convinced it makes a real difference unless a person has a unique setting.

Yes, as I'm doing more research, I'm finding that I would prefer to invest in markets that I know personally, so as not to rely on external variables completely.

I have personally been the guy who hasn't pulled permits and got caught...by far one of the worst experiences of my investing career.

Do you have a 501c3 that you operate under (and rent the house from yourself), or do you purchase homes with an LLC or personal name, and run as a regular business? 

Also, you don’t need a business license just to look at properties, but if you buy a bigger property, like a multi-family unit, you might need a certificate of occupancy, depending on the local rules.For business trips, most expenses can be deductible, but if it’s part personal and part business, you can only deduct the business portion.

Maybe the section 8 person can help advise you, but I'm certain they will give a disclaimer with anything they say that you still need to consult your own lawyer or read the rules.

If you do decide to do mailer(s), then I would advise you to personalize the card and do a handwritten note. 

Looking forward to meeting you all virtually sometime, or in person on a visit to PT. 

If you and another person own a piece of real estate as tenants in common then you both own real estate. 

Whichever direction you go, be sure to work with folks who understand this and gives you the confidence to take reasonable action - I'd personally take an okay investment and weather the storm for a few years that will eventually perform well, and do that each year - rather than take 3 years to wait for the best deal possible.