Sharing the potential challenges he might face, rather than discouraging him, allows him to assess whether he’s ready to tackle them, increasing his chance of success.We’re all here to help each other grow, right?

If it’s a larger or commercial property, consider conducting an environmental check to assess potential risks like contamination or flooding.It’s also important to request a full property disclosure from the seller, which may include known issues or defects with the property.

I don't know if the returns would be there unless you are doing something at a scale where you have half a dozen to a dozen STRs in the same general proximity. 

Also, I know those who’ve gotten hit with special assessments that wiped away cash flow and some. 

Regarding Chicago, the 2024 property tax re-assessment in Cook County should cause some inventory to hit the market, specifically on the mixed-use and multi-family side of things which will be hit especially hard.

It won’t be possible to assess the damage as wires and wood are behind the wall.

If you didn't buy solely off the fact you needed to 1031, then did tax re-assessment get you?

After going to the board of equalization to reconsider the value of the property, the came back with a updated assessed value of $8,000 and some change.

Furthermore  once the 1031 intermediary get their cut and you also pay two sets of closing costs ( buyers now have to pay closing costs in some states ) as opposed to just one closing cost ( if not doing the 1031) it might be a “half a dozen vs 6 of the other “ scenario .Also one of the turn offs to the 1031 exchange is the interest rate will be much higher with todays rates especially since we would have to get an investment property loan which are higher than “ primary residence “ loans ..Will probably lower the rent asap ( have one more showing ) and then put it on the market .Thanks for the great advice Christian 

no I have not purchased the home yet -but I’m educated and working with a realtor who understands the process.1st- you have to be a recipient of a section 8 housing choice voucher /in the program and in good standing2nd you need to be in the rental unit and in the program for a year minimum3rd you must to be in a “participating housing authority” or PHA  because not all Housing Authority’s participate in this rent voucher -to -home mortgage voucher program4th it may ( or may not) require recipient  enrolling in an additional sub program called families for Self Sufficiency ( FSS) which has a class that teaches voucher holders how to use the voucher for a mortgage payment5th I’m working with a realtor who understands the process - has used it for dozens if not hundreds of clients. it’s going to be VERY hard for anyone unfamiliar with government processes  to get through it successfully. note I’m also utilizing  first time savings plans IDA‘s and local first time homebuyer grants and a USDA 502 direct low income Rural loan. and my own funds.All aid mentioned can be “stacked” to lower mortgage & create long term affordability.