Shoot me a DM if you want some help with finding a condo or house with a low rate that's on market.

The rules are designed to prevent related parties from engaging in exchanges that shift high basis property for low basis property, followed by a sale of the low basis property, effectively "cashing out" without recognizing gain.If you sell a property to a related party as part of a 1031 exchange, both you and the related party must hold the exchanged properties for at least two years following the exchange.

High credit scores and low DTI are often required…and these take much longer than I first thought…Navy might take 45 days to get through the gauntlet.  

It allows you to take advantage of a low down payment loan.

So assuming your son has low debt, then he should be able to qualify for a house in the low $300K range. 

I've never really done a deep dive in analyzing the area because it is a retirement community, median income is very low, and there arent a lot of jobs in the area.

Consider a HELOC for value-added BRRRRs or flips if you have a low interest rate.

Target Low Vacancy RatesChicago neighborhoods like Lakeview and West Town boast low vacancy rates, meaning fewer empty months.

Some of the materials we choose and asked him to pick up (such as flooring) he replaced with low quality materials, I assume to keep more of our money for himself. 

If I ever run low on reserves, I can easily transfer funds from my personal to rental account.