He then became the department chair, and then the interim dean for the business school. 

I'd be shocked if they spent more than $5k on bed, mattress, couch, chair, tables, linens, and kitchen items.We didn't have to pay tax on the rental because it was over 30 days (33 to be exact), but that will differ across municipalities.The opportunity for STR operators is to provide an improved experience than what the larger corporate lease companies are doing.

What you are describing  would be a self-dealing prohibited transaction that would void the IRA.There can be no direct or indirect transactions between an IRA and a disqualified party. 

Typically your Governing Documents will require adhering to RRO procedures, although the level of formality is generally up to the discretion of the Chair in smaller organizations.

I built/remodeled custom homes and the customers would bring in tables/chairs and all their friends, and sit around and drink and critique the work.....

McGaughe" on the subject.There are state and federal laws to consider.From the SEC website:The federal securities laws define the term accredited investor in Rule 501 of Regulation D as:a bank, insurance company, registered investment company, business development company, or small business investment company;an employee benefit plan, within the meaning of the Employee Retirement Income Security Act, if a bank, insurance company, or registered investment adviser makes the investment decisions, or if the plan has total assets in excess of $5 million;a charitable organization, corporation, or partnership with assets exceeding $5 million;a director, executive officer, or general partner of the company selling the securities;a business in which all the equity owners are accredited investors;a natural person who has individual net worth, or joint net worth with the person’s spouse, that exceeds $1 million at the time of the purchase, excluding the value of the primary residence of such person;a natural person with income exceeding $200,000 in each of the two most recent years or joint income with a spouse exceeding $300,000 for those years and a reasonable expectation of the same income level in the current year; ora trust with assets in excess of $5 million, not formed to acquire the securities offered, whose purchases a sophisticated person makes.The aforementioned is personal opinion and none of the content should be construed a binding offer or agreement.

I had a conversation with one of the directors of Tax Sale, and she told me that the third sale list was "the dogs of the dogs". 

For summer renters you go in, do a thorough clean and replace, put back the linens, towels, comforters, wine glasses, add the beach chairs etc. 

In our location it is 2 beach chairs & 1 umbrella set up on the beach & reserved for the guests of your property each day from March 1 - October 31.

These buisnesses have provided a very modest income - my primary income comes as corporate man, I have worked with both AT&T and Verizon as a field sales director, as a district and regional manager.