Zoning & ADU ConsiderationsChicago’s ADU Ordinance applies if you create an additional dwelling unit beyond the existing count.If you stay at 2 units total (just shifting one unit partially to the basement), you likely don’t trigger ADU rules—but confirm with zoning since each ward can interpret things differently.If you want to eventually rent the basement as its own apartment, you will need proper zoning, permits, and a second exit per Chicago code.3.

(Plus, the Big Creek Greenway is excellent for cycling)My background is in technology and data analytics, primarily in healthcare software.

I got to about 10 properties before I started paying for softwares. 

. $370k owed), which gives you options.If you want to stretch every angle, I’d:Call PennyMac and ask directly if the note is assumable.Talk with an estate attorney to confirm what’s possible under the transfer.Run the numbers on a refi vs. paying off a chunk to keep payments low.Wish I had a magic answer, but that’s the reality with inherited VA loans; I’m sorry for your loss and I hope this helps you a bit, I sent you a DM on BP and hope you can assist. 

@Samuel GunawanBRRRR numbers can look messy at first, but I keep it simple: total all-in costs (purchase + rehab + closing/holding), confirm ARV with comps, then check if the bank’s 70–75% refi covers most of those costs.

Also, confirm local STR regulations are stable and transferable.

Main benefits to 20% down are:- you're more likely to cashflow - the loan may be easier to obtain and can close faster than FHA- sellers can be more intrigued by higher down payment offersMain benefits to lower down payment househacking:- start building equity sooner vs. waiting to boost savings- could get a lower interest rate - lower loan requirements vs. conventional*Speak with a lender to confirm best options for your situation and future goalsAll the best!

Confirm—explicitly—that the offering is 1031-eligible as a TIC or DST; “syndication” is a broad term and a lot of deals are LP/LLC only.

There are many posts on BiggerPockets about landlord software, but here’s a consolidated overview.Must-have features landlords mention most often: online payments, full accounting, 1099 tracking and e-filing, tenant portal, owner portal (if you manage for others), work order tracking, vacancy syndication, online leases, and tenant screening.

@Jules Aton we agree with Account ClosedA reputable PMC should be using Property Management software to properly manage rentals.Every PMC sofware we've looked at has built-in accounting with the ability to generate invoices.