I am not an attorney nor a landlord, but it seems like it would be a safe & smart choice to let the tenant know someone will be coming on to their property.

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The penalties for failure to comply if the safe harbor is revoked far outweigh the cost of compliance from the 1st transaction.

I would still collect rent monthly if I were you just to be safe unless the rules are different in CT.

Further, the only way to insure that your offering of a security is an exempt private offering, is to comply with the safe harbor exemption of Rule 504, or if an intrastate offering a similar setup at the state level.As a practical matter, the issue for the small, occasional deal maker would only arise if an investor lost money, sued the deal maker, and claims the sale of an unregistered security with out the private offering exemption.  

All contracts, options, or other devices not based upon a substantial consideration, or that are otherwise employed to permit an unlicensed person to sell, lease, or let real estate, the beneficial title to which has not, in good faith, passed to such party for a substantial consideration, are hereby declared void and ineffective in all cases, suits, or proceedings had or taken under this chapter; however, this section shall not apply to irrevocable gifts, to unconditional contracts to purchase, or to options based upon a substantial consideration actually paid and not subject to any agreements to return or right of return reserved.

A It certainly won't get your ball rolling fast but many of my clients used this method to get started in investing so I think its a safe way of going about it, especially with you living there.

If not, do a search on BP for their tenant screening and free rent collection website.While I do not believe they have an app (yet), you can access their website on your mobile device.

Until being made clear, I've decided to stick to areas where I feel absolutely safe taking the title on and then selling.

If you are offering a clean, safe place for the students to live that their parents feel good about you should have no problem keeping it occupied.