You might be able to get around the fact your entity owns the property by either transferring the property back into your personal name or by some personal guarantee or cross-collaterization agreement.

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.

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

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

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.

Do you have a personal connection to either of those cities/markets?

Personally (as a STR-focused REALTOR), I would never give you numbers and tell you you can hit them. 

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

Here is my favorite (among several others, just as hysterical) part of this case:"...Petitioner’s testimony that neither he nor his son used his personal bedroom,living room, or kitchen for personal reasons strains credibility.