I am considering converting to a long term rental but thought that mid term might also be a good approach as well considering the home is fully furnished.

I am actually thinking of converting it to an Airbnb rental.

I can convert the garage into a one or two-story extra unit on the property.  

@Brad Kanouse,I believe this is a duplicate of this post:https://www.biggerpockets.com/forums/311/topics/1210256-usin...But regardless, here is my answer:If you take a distribution from an IRA - it will be subject to taxes and penalties.You can convert your IRA into a "Self-directed IRA" and have the IRA buy the property, in this case you are not the owner, the IRA is.

Your starting depreciable basis should have been the LOWER of what you paid or the FMV in 2010 when you converted it to a condo. 

Our main carrier policy converts to vacant dwelling policy at completion for duration of term and can be renewed on case by case basis if unfinished or unsold.  

And I’m wondering why more ppl don’t convert to this type of system.

This defers capital gains and depreciation recapture taxes on the sale of your fourplex.After converting it into your primary residence, you may qualify for the primary residence capital gains exclusion ($250K single/$500K married), but only for appreciation after the conversion; gains from the rental period remain taxable.

He may be actually speaking about a "Wrap".Find out if actual ownership converts to youMake sure you have a title reportYou may want to pay for an appraisal and an inspectionMake sure you use an escrow company or an attorney to do the transaction Hi Ken!

For a rental property, the gain is subject to capital gains tax (15-20%) and depreciation recapture tax (up to 25%) on any depreciation claimed, unless the proceeds are reinvested.To minimize taxes, consider reinvesting the sale and insurance proceeds into another property under §1033 or converting the property to a rental before selling to claim depreciation deductions.This post does not create a CPA-Client relationship.