UPDATE:  Just chatted with the city and learned that variances have a high threshold for approval.  

I would shoot him regular updates to keep him in the loop.

Gifting equity in a house may be more trouble than it is worth if you are not near the life-time exclusion1) Potentially having to get the property appraised everytime an equity is gifted2) Having a title company update the title every time3) Exemption of the gift tax return is normally for cash gifts below the annual gift tax exclusion, you may still need to file if you gift non-cash4) If there is partial ownership over several years, having to properly pro-rate certain items such as real estate taxes, mortgage interest and rental income if the property is a rentalBest of luck 

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

Are there any house at that price point that would rent for $1200-1500/ month with 20k worth of updating?"

Thoughts and updates on Southern Impression Homes and SunCoast.  

I'm fairly handy, but just to balance things with my 9-5 job, focusing on something that just needs superficial updates or something nearly turn-key is probably best. 

Good luck and keep us updated on how it goes. 

highlight_post=6413855&page=1https://www.biggerpockets.com/forums/92/topics/929410-rent-to-retirement-updates?

Quote from @Jordan Gibbs: Quote from @Lindsey Pinkham: Any update on if anyone has done this program?!