A revocable living trust is another option for privacy and asset protection.Avoid gifting the property before death, as this would pass the original purchase price as the cost basis, creating a large capital gains tax liability upon sale.If the property is Subject A’s homestead, ensure the correct titling to maintain Florida’s homestead protection for Subject B.This post does not create a CPA-Client relationship.

Think I better clarify - this isn't an altruistic attempt to help VRBO 😄, but rather a hope that it might result in a higher overall booking rate if both platforms perform at a high level

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

This may be controversial but it seems like you would be saving a lot of money at the moment given your reduced living costs.

Selling at FMV avoids the gift tax but provides your child with a higher tax basis, reducing their future capital gains liability.A better strategy for selling below FMV is to sell the house at FMV on an installment note, then forgive interest and principal annually up to the gift tax exclusion amount.

These properties are generally in high demand, but on a positive there will be drastically less new inventory of competing rental properties. 

In my understanding, I thought most high quality syndication opportunities were open to accredited investors only.

@David YoungRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

They don’t factor in the quality of renovations or unique property features, which are critical when determining a true ARV.

Likely will reduce to whatever market rent is on 1007 report, if the Section 8 income is higher than market.