Some thoughts to consider:If you sell now, you are unlikely to pay capital gains taxes as your first 250k (500k if married and filling jointly) aren't reported.Doing your first rental remotely is undesirable without 1.)

The parent must file a gift tax return annually, and any remaining balance is included in the estate.If the home was your primary residence for at least 2 of the last 5 years, you may exclude up to $250,000 ($500,000 if married filing jointly) of capital gains from taxes.

Keep track of 3 buckets.1) Owner occupied portion - potential deductions for schedule A2) Tenant occupied portion - potential deductions for schedule E3) Jointly occupied portion - likely prorated for both schedules.There are nuances to this, so I recommend looking for a tax pro who can coach you on this. 

He also offers coaching where you joint venture on deals.

Might have to do a joint venture. 

The parties will jointly appoint an acceptable mediator and will share equally in the cost of such mediation.

Joint tax return?  

Everything was a joint decision.

I have the opportunity to help a family member be part of a joint venture with them putting the down payment down.  

If you continue filing taxes jointly the income you realize from your separate property will still need to be explained and redacted, regardless of the type of entity holding the real estate.