Basically, I'm trading $300-$500 per month for this benefit.But, lenders want interest first, principle later.

Since this post didn't get any replies, I'm going to reply with what I ended up doing incase it helps anyone else later.

I figured I’d “get to it later.”The day after closing, the former owner broke in and set a small fire out of anger.

For your first deal, I would recommend just get a good deal that makes sense, close in your personal name as you can often put it under a trust or LLC later (depending on the lender and loan program used to buy) if you determine that to be the best course of action for you.  

You’ll also want to let your CPA know, since how you treat the transfer (as a sale vs. a disregarded transfer) can vary depending on how the LLCs are structured (single-member, disregarded, partnership, etc.).You did the right thing by moving it into the holding LLC once you decided to keep it — that’s a good habit for scaling later.

And if you plan to sell some units and keep one, look into a condo conversion or parcel split so you can deed them separately later.

Hey everyone,I’m comparing two 3-unit properties in Chicago and could use some insight from local investors.Option 1 – South Side (near Woodlawn area):Priced around $830KModern finishes, newer construction styleCurrent rents around $2,195, $2,000, and $2,000The area has a lot of new developments and new 3-flats going upMy concern: with so many new buildings being added, there’s likely going to be more rental competition, and property taxes may jump once reassessments catch up to all the new construction.Option 2 – Pilsen area:Priced around $735KAlso modern updates but smaller units (two 2-beds and one 3-bed)Taxes are currently low, but likely because the property hasn’t been reassessed since the recent renovationsThe area feels more established, with strong tenant demand and characterSo I’m weighing the growth potential and higher risk in the newer South Side market versus the more stable rents and potentially upcoming tax adjustments in Pilsen.Would you lean toward the newer-construction area with possible tax jumps but longer-term appreciation upside, or the lower-tax, established neighborhood that might get hit with reassessment later?

Quote from @Jean Pierre Jabo: my wife and i bought a unit last year in 2024. home is a 4 bd 2 bth, comes with a detached ADU unit thats 1 bed one bath with separate backyard that we currently rent for $1545 longterm. our interest rate is high, 7.1%. our mortage is about 3600 but adding PMI and other costs its total of $4k/month. we both make a combined income of $220k. should we try to move to another primary residence home about $480k and rent out our current main home for about 2300-2400 (fair market pricing for the area). or should we stay in our home and refinance and live there for a year and then move later? 

It saves you headaches (and IRS letters) later.2.

You might also consider how each option affects your long-term strategy, does refinancing the first property give you more flexibility to buy additional properties later, or does acquiring a second property now better position you for future appreciation?