The two are almost entirely different markets in terms of price points, returns, tenant quality, and overall investing strategy.

Multi-family properties many times provide a better return per square foot than single family, which would be to your advantage as well.As long as you're mindful of the reinvestment requirements and purchase at least as much as you sold and use all of the proceeds, you shouldn't have any issues with this strategy.

I would get together with your realtor, have them tour your property and then run comps to see what the value add would be, then simply pencil it out to determine the return. 

Not only does it hurt the returns, it is a very attractive target for ambulance-chasing lawyers and title fraud.  

For rentals, focus on cash flow and metrics like cap rate (target 8%-10%) or cash-on-cash return.

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 

You need to understand how to drive the Net Operating Income to produce a good solid return. 

From an operational standpoint you might also want to consider the cost of any extra tax returns that are needed by the entity as well as any extra accounting fees.Good Luck!

I can’t imagine the returns you would have to generate. 22% federal tax, plus 8% state tax, plus 10% penalty.

It’s one of the few places where you can realistically achieve solid returns without needing a massive upfront investment.If you’re open to exploring other markets, Detroit might be worth considering.