Has a brand new roof and all the mechanicals are updated.

They are using the entire rental, why not make them responsible for fixing/replacing your roof or HVAC as well?!?

Which means even if you had an inspector there on that day, it would be a few days before you could get coverage (assuming there were no issues needing remedying first, like an old water heater, roof, etc.).  

We prettied her up, gave her a new sewer, new roof, new garage roof, cleared out a ton of junk, and put this into production in 2020.

Hi Chicagoland BP community! Looking for some referrals for contractors who could come and check a finished basement that had minor flooding after the recent storm in Chicago (Avondale). I didn't get a lot of water an...

Learn the ropes, get yourself a roof over your head and take advantage of best rates and low downpayment. 

For example, roofing, painting, cabinets, flooring, electrical, plumbing, HVAC, etc. 

But I have been looking into splitting the duplex into two condos (yes I know it is a lot of work) and I could probably get 325-350k for each, netting me 650-700k.Number:* Mortgage interest 2.5%* Mortgage principle 240k* PITI $2100/month* Rent 2200/month (current tenant on a two year lease)* Potential rent on my side $2400/month * 100k HELOC at 11% (fixed) (not currently being used)* est additional cost to split the dueplex 75-100k (conservative, probably less)     *new siding 30k (just put on a new roof this year)     *legal 10-15k     *fire proofing 15k     * 15-40k for stuff I am not aware of or underestimated on* some of the appreciation is external from the home     *big grocery store put in 3min away     * newly paved road in front of my house     *a building that was falling down across the street has been torn down          * Still a vacant lot with the foundation exposed and fencing around it (so more local improvements are on the way)Part of me wants to take the money and run but man I love that 2.5% interest rate and the $2000/month cash flow (including taxes and capx)I have thought about 1031 exchanging into more rentals, but I would like to pivot into storage units.

Your traditional bank in most instances is going to take the loan and resell it on the secondary market.For House Hacking, my favorite concept is  purchasing a duplex, triplex or quadplex, you accomplish 2 things in 1 step, you get a roof over your head, and at a minimum you get someone else to help pay for your mortgage, and when its time to move out, you already have your 1st investment property under your belt.

If so, how did you mitigate all the potential issues that come with have so many different people under one roof?