This was the hardest undertaking of my career.

We changed some furniture and did some minor redecorating.

A few examples of the many lines that would be crossed by doing this (I stopped looking for examples after around Article 10, I'm sure there are my others):Article 1: When serving a buyer, seller, landlord, tenant or other party in a non-agency capacity, REALTORS® remain obligated to treat all parties honestly.Article 2: REALTORS® shall avoid exaggeration, misrepresentation, or concealment of pertinent facts relating to the property or the transaction.Article 4: REALTORS® shall not acquire an interest in or buy or present offers from themselves, any member of their immediate families, their firms or any member thereof, or any entities in which they have any ownership interest, any real property without making their true position known to the owner or the owner’s agent or broker.Article 5: REALTORS® shall not undertake to provide professional services concerning a property or its value where they have a present or contemplated interest unless such interest is specifically disclosed to all affected parties.Article 7: In a transaction, REALTORS® shall not accept compensation from more than one party, even if permitted by law, without disclosure to all parties and the informed consent of the REALTOR®’s client or clients.Close on the deal yourself or broker it to someone else who can.

Not only does this sound like a massive under taking, but I would be curious what the cost is.  

Moving forward with this in mind it might be worth determining if this is a live in care giver that is simply an individual who has decided to undertake this career path that needs fully screened just as any other tenant- or has this person been hired through an agency, where screening ahs already transpired?

Is this generally a big undertaking or fairly simple.

Once you have owned it for 5 years and lived in it at least 2 (or if it's time to redecorate) sell it and take the partial primary exemption. 

This is a sizable undertaking and if you have not done this before, well what could possibly go wrong?

I'm seeking the 80% as I know that will free up the cash desired to undertake my next property + sufficient liquid reserves.  75% may get me there, but not positive. 

I have about $10k to put towards a down-payment and an increasing variety of loan program options from some first time homebuyer grants (duplex eligible) as well as a mission-driven hard money lending program that's focused on getting locals to undertake scattered-site rehab and to curb gentrification from outside investment and yuppie tenants; then there's FHA 203k which I've heard can be alot to manage for a first-timer.